CN106867518A - A kind of luminous organic material for launching green glow and preparation method thereof - Google Patents
A kind of luminous organic material for launching green glow and preparation method thereof Download PDFInfo
- Publication number
- CN106867518A CN106867518A CN201710044923.0A CN201710044923A CN106867518A CN 106867518 A CN106867518 A CN 106867518A CN 201710044923 A CN201710044923 A CN 201710044923A CN 106867518 A CN106867518 A CN 106867518A
- Authority
- CN
- China
- Prior art keywords
- bis
- preparation
- diazosulfide
- organic material
- luminous organic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/14—Thiadiazoles; Hydrogenated thiadiazoles condensed with carbocyclic rings or ring systems
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Luminescent Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The present invention provides a kind of luminous organic material for launching green glow and preparation method thereof, is related to technical field of organic luminescence materials.Luminous organic material of the present invention is 4,7 two (3,5 di-tert-butyl-phenyl) 2,1,3 diazosulfide.The luminous organic material of present invention transmitting green glow is a kind of pure colourity, simple structure, the green light material that fluorescence quantum yield is higher, dissolubility is good, it is preferable green light luminescent material, there is potential application in organic electroluminescence display field, and preparation method operating process is simple, reaction condition is gentleer, product separating-purifying is simple, and yield is higher.
Description
Technical field
The present invention relates to technical field of organic luminescence materials, it is related to a kind of luminous organic material for launching green glow and its preparation
Method.
Background technology
Organic Light Emitting Diode is because its self-luminous, all solid state, wide viewing angle, fast response time, driving voltage are low, low energy
Consumption, efficiency high, it is flexible many advantages, such as, as research focus.To realize full-color fluorescent emission, red, green, blue three primary colours
Fluorescent material it is essential in organic luminescent device field.
2,1,3- diazosulfides are often applied to field of photovoltaic materials as electron donor, due in novel optical and
Potential application in electronics material so that this material is widely closed in terms of photoelectricity and electroluminescent organic material
Note, more red illuminating material is emerged based on this structure.The organic molecule of other D- π-A configurations is due to its intramolecular charge
Transfer (ICT) can produce quantum efficiency compound higher, just be widely used in luminous organic material aspect.
From the point of view of the situation of current research, blue light material, red light material research are numerous, but high efficiency, colourity is pure, structure
Simple green light material is less, and this limits the development of organic luminescent device to a certain extent.
The content of the invention
In view of the shortcomings of the prior art, the present invention provides a kind of luminous organic material for launching green glow and preparation method thereof, solution
Determine in the prior art the technical problem that high efficiency, colourity are pure, simple structure green light material is less.
To realize object above, the present invention is achieved by the following technical programs：
A kind of luminous organic material for launching green glow, the luminous organic material is (3, the 5- di-tert-butyls of 4,7- bis-
Base) -2,1,3- diazosulfide, with the structure shown in formula (I)：
A kind of preparation method of the luminous organic material for launching green glow, comprises the following steps：
S1, by 2,1,3- diazosulfide is added in the flask equipped with 40-60mlHBr solution, then to 25- is added dropwise in flask
35mlHBr solution, is stirred when being added dropwise, and 100-200 DEG C of backflow 4-8h is heated to after dripping, and cooling adds the sulfurous of saturation
Acid sodium solution, refilters, recrystallizes and obtain 4,7- bis- bromo- 2,1,3- diazosulfide；
S2, under nitrogen atmosphere, to equipped with toluene, K2CO34,7- bis- bromo- 2,1,3- benzo are added in the flask of the aqueous solution
Thiadiazoles, 3,5- di-t-butyls phenyl boric acid, Cs2CO3, tetra-triphenylphosphine palladium, be heated to temperature for 100-150 DEG C, react 10-
36h, cooling, obtains reactant mixture；
S3, by obtained in step S2 reactant mixture extract 2-4 times, then wash, dry, vacuum distillation, obtain crude product,
Elute again, purify, obtain 4,7- bis- (3,5- di-tert-butyl-phenyl) -2,1,3- diazosulfide.
Preferably, 4,7- bis- bromo- 2 described in step S2,1,3- diazosulfide and 3,5- di-t-butyl phenyl boric acid mole
Than being 1：2-4.
Preferably, 4,7- bis- bromo- 2 described in step S2,1,3- diazosulfide is 1 with the mol ratio of tetra-triphenylphosphine palladium：
0.02-0.05。
Preferably, temperature is heated to described in step S2 for 120-140 DEG C.
Preferably, the reaction time described in step S2 is 20-30h.
Preferably, cooled down described in step S1, step S2 and be cooled to room temperature.
Preferably, the step S3 is by obtained reactant mixture CH2Cl2Extraction three times, organic layer with salt water washing it
The crude product for obtaining afterwards, then using crude product dichloromethane and petroleum ether as eluent, then carry out silica gel column chromatography and carry
It is pure, you can.
The present invention 4,-two (3,5- di-tert-butyl-phenyls) -2, the synthetic route of 1,3- diazosulfide is as follows：
The present invention provides a kind of luminous organic material for launching green glow and preparation method thereof, and advantage exists compared with prior art
In：
The luminous organic material of present invention transmitting green glow is the benzo thiophenes two of 4,7- bis- (3,5- di-tert-butyl-phenyl) -2,1,3-
Azoles, the green light material that the material is a kind of pure colourity, simple structure, fluorescence quantum yield is higher, dissolubility is good is preferably green
Light luminescent material, has potential application in organic electroluminescence display field；
The preparation method operating process of the luminous organic material of present invention transmitting green glow is simple, and reaction condition is gentleer,
Product separating-purifying is simple, and yield is higher, and yield can reach 90%, and prepared green light material belongs to the luminous material of small molecule
Material, has good application prospect in luminescent device.
Brief description of the drawings
Fig. 1 be green light material of the present invention 4,7- bis- (3,5- di-tert-butyl-phenyl) -2,1,3- diazosulfide is in toluene
Fluorescence emission spectrogram of compound；
Fig. 2 is green light material of the present invention 4, and 7- bis- (3,5- di-tert-butyl-phenyl) -2, the nuclear-magnetism of 1,3- diazosulfide is total to
Shake hydrogen spectrogram.
Specific embodiment
To make the purpose, technical scheme and advantage of the embodiment of the present invention clearer, with reference to the embodiment of the present invention pair
Technical scheme in the embodiment of the present invention is clearly and completely described, it is clear that described embodiment is a part of the invention
Embodiment, rather than whole embodiments.Based on the embodiment in the present invention, those of ordinary skill in the art are not making wound
The every other embodiment obtained under the premise of the property made work, belongs to the scope of protection of the invention.
Embodiment 1：
The present embodiment 4,7- bis- (3,5- di-tert-butyl-phenyl) -2, the preparation method of 1,3- diazosulfide, including it is following
Step：
S1, in the round-bottomed flask of 250ml be equipped with 50mlHBr solution (48%), add 3g (22.00mmol) 2,1,3-
Diazosulfide, 30ml HBr solution (48%), the round bottom for dropping to are dissolved in constant pressure funnel by 10g (65.00mmol) Br2
In flask, it is stirred vigorously when being added dropwise, 150 DEG C is heated to after all dripping and is flowed back 6 hours, reaction is cooled to room after terminating
Temperature, adds the sodium sulfite solution of saturation, the solid filtering that will be separated out, and flaxen crude product is obtained, by this crude product in work
Property charcoal exist under conditions of be recrystallized to give 4,7- bis- bromo- 2 with n-hexane, 1,3- diazosulfide 6.08g, white solid, meter
It is 94% to calculate yield；
S2, under nitrogen protection, to equipped with 50ml toluene, the 250ml of the 25ml K2CO3 aqueous solution (8.0g, 57.9mmol)
Two mouthfuls of round-bottomed flasks in add 1.94g (6.6mmol) 4,7- bis- bromo- 2,1,3- diazosulfides, 3.096g (13.2mmol)
3,5- di-t-butyl phenyl boric acids, 2g (6.1mmol) Cs2CO3,0.289g (0.25mmol) tetra-triphenylphosphine palladium, are heated to temperature
It is 100 DEG C, reacts 24h, cooling obtains reactant mixture；
S3, reactant mixture obtained in step S2 is poured into water, uses CH2Cl2Extraction 3 times, the organic layer salt that will be obtained
After water washing, then use anhydrous Na2SO4It is dried, vacuum distillation afterwards removes solvent, obtains crude product, and crude product is used into two
Chloromethanes and petroleum ether are eluted as the solvent of eluant, eluent, silica gel column chromatography purification, obtain (3, the 5- di-t-butyls of 4,7- bis-
Phenyl) -2,1,3- diazosulfide 2.98g.Obtained 4,7- bis- (3,5- di-tert-butyl-phenyl) -2,1,3- diazosulfide is
Green solid.Yield 88%.1HNMR(400MHz,CDCl3),δ[ppm]:7.81-7.78(m,6H),7.55-7.52(t,2H),
1.42(s,36H)。
By 4,7- obtained in the present embodiment bis- (3,5- di-tert-butyl-phenyl) -2,1,3- diazosulfide does fluorescence emission
Spectrum experiment and nuclear magnetic resonance experiment, as a result as depicted in figs. 1 and 2.
Embodiment 2：
The present embodiment 4,7- bis- (3,5- di-tert-butyl-phenyl) -2, the preparation method of 1,3- diazosulfide, including it is following
Step：
S1, in the round-bottomed flask of 250ml be equipped with 60mlHBr solution (48%), add 3g (22.00mmol) 2,1,3-
Diazosulfide, 35ml HBr solution (48%), the round bottom for dropping to are dissolved in constant pressure funnel by 10g (65.00mmol) Br2
In flask, it is stirred vigorously when being added dropwise, 200 DEG C is heated to after all dripping and is flowed back 8 hours, reaction is cooled to room after terminating
Temperature, adds the sodium sulfite solution of saturation, the solid filtering that will be separated out, and flaxen crude product is obtained, by this crude product in work
Property charcoal exist under conditions of be recrystallized to give 4,7- bis- bromo- 2 with n-hexane, 1,3- diazosulfide 6.08g, white solid, meter
It is 92% to calculate yield；
S2, under nitrogen protection, to equipped with 50ml toluene, the 250ml of the 25ml K2CO3 aqueous solution (8.0g, 57.9mmol)
Two mouthfuls of round-bottomed flasks in add 1.94g (6.6mmol) 4,7- bis- bromo- 2,1,3- diazosulfides, 6.192g (26.4mmol)
3,5- di-t-butyl phenyl boric acids, 2g (6.1mmol) Cs2CO3,0.587g (0.50mmol) tetra-triphenylphosphine palladium, are heated to temperature
It is 120 DEG C, reacts 30h, cooling obtains reactant mixture；
S3, reactant mixture obtained in step S2 is poured into water, uses CH2Cl2Extraction 2 times, the organic layer salt that will be obtained
After water washing, then use anhydrous Na2SO4It is dried, vacuum distillation afterwards removes solvent, obtains crude product, and crude product is used into two
Chloromethanes and petroleum ether are eluted as the solvent of eluant, eluent, silica gel column chromatography purification, obtain (3, the 5- di-t-butyls of 4,7- bis-
Phenyl) -2,1,3- diazosulfide 2.88g.Obtained 4,7- bis- (3,5- di-tert-butyl-phenyl) -2,1,3- diazosulfide is
Green solid.Yield 85%.1HNMR(400MHz,CDCl3),δ[ppm]:7.81-7.78(m,6H),7.55-7.52(t,2H),
1.42(s,36H)。
Embodiment 3：
The present embodiment 4,7- bis- (3,5- di-tert-butyl-phenyl) -2, the preparation method of 1,3- diazosulfide, including it is following
Step：
S1, in the round-bottomed flask of 250ml be equipped with 40mlHBr solution (48%), add 3g (22.00mmol) 2,1,3-
Diazosulfide, 25ml HBr solution (48%), the round bottom for dropping to are dissolved in constant pressure funnel by 10g (65.00mmol) Br2
In flask, it is stirred vigorously when being added dropwise, 100 DEG C is heated to after all dripping and is flowed back 4 hours, reaction is cooled to room after terminating
Temperature, adds the sodium sulfite solution of saturation, the solid filtering that will be separated out, and flaxen crude product is obtained, by this crude product in work
Property charcoal exist under conditions of be recrystallized to give 4,7- bis- bromo- 2 with n-hexane, 1,3- diazosulfide 6.08g, white solid, meter
It is 95% to calculate yield；
S2, under nitrogen protection, to equipped with 50ml toluene, the 250ml of the 25ml K2CO3 aqueous solution (8.0g, 57.9mmol)
Two mouthfuls of round-bottomed flasks in add 1.94g (6.6mmol) 4,7- bis- bromo- 2,1,3- diazosulfides, 3.87g (16.5mmol) 3,
5- di-t-butyls phenyl boric acid, 2g (6.1mmol) Cs2CO3,0.289g (0.25mmol) tetra-triphenylphosphine palladium, being heated to temperature is
130 DEG C, 24h is reacted, cooling obtains reactant mixture；
S3, reactant mixture obtained in step S2 is poured into water, uses CH2Cl2Extraction 3 times, the organic layer salt that will be obtained
After water washing, then use anhydrous Na2SO4It is dried, vacuum distillation afterwards removes solvent, obtains crude product, and crude product is used into two
Chloromethanes and petroleum ether are eluted as the solvent of eluant, eluent, silica gel column chromatography purification, obtain (3, the 5- di-t-butyls of 4,7- bis-
Phenyl) -2,1,3- diazosulfide 3.05g.Obtained 4,7- bis- (3,5- di-tert-butyl-phenyl) -2,1,3- diazosulfide is
Green solid.Yield 90%.1HNMR(400MHz,CDCl3),δ[ppm]:7.81-7.78(m,6H),7.55-7.52(t,2H),
1.42(s,36H)。
Embodiment 4：
The present embodiment 4,7- bis- (3,5- di-tert-butyl-phenyl) -2, the preparation method of 1,3- diazosulfide, including it is following
Step：
S1, in the round-bottomed flask of 250ml be equipped with 50mlHBr solution (48%), add 3g (22.00mmol) 2,1,3-
Diazosulfide, 30ml HBr solution (48%), the round bottom for dropping to are dissolved in constant pressure funnel by 10g (65.00mmol) Br2
In flask, it is stirred vigorously when being added dropwise, 150 DEG C is heated to after all dripping and is flowed back 6 hours, reaction is cooled to room after terminating
Temperature, adds the sodium sulfite solution of saturation, the solid filtering that will be separated out, and flaxen crude product is obtained, by this crude product in work
Property charcoal exist under conditions of be recrystallized to give 4,7- bis- bromo- 2 with n-hexane, 1,3- diazosulfide 6.08g, white solid, meter
It is 94% to calculate yield；
S2, under nitrogen protection, to equipped with 50ml toluene, the 250ml of the 25ml K2CO3 aqueous solution (8.0g, 57.9mmol)
Two mouthfuls of round-bottomed flasks in add 1.94g (6.6mmol) 4,7- bis- bromo- 2,1,3- diazosulfides, 4.644g (19.8mmol)
3,5- di-t-butyl phenyl boric acids, 2g (6.1mmol) Cs2CO3,0.3468g (0.30mmol) tetra-triphenylphosphine palladium, are heated to temperature
It is 140 DEG C, reacts 36h, cooling obtains reactant mixture；
S3, reactant mixture obtained in step S2 is poured into water, uses CH2Cl2Extraction 3 times, the organic layer salt that will be obtained
After water washing, then use anhydrous Na2SO4It is dried, vacuum distillation afterwards removes solvent, obtains crude product, and crude product is used into two
Chloromethanes and petroleum ether are eluted as the solvent of eluant, eluent, silica gel column chromatography purification, obtain (3, the 5- di-t-butyls of 4,7- bis-
Phenyl) -2,1,3- diazosulfide 2.78g.Obtained 4,7- bis- (3,5- di-tert-butyl-phenyl) -2,1,3- diazosulfide is
Green solid.Yield 82%.1HNMR(400MHz,CDCl3),δ[ppm]:7.81-7.78(m,6H),7.55-7.52(t,2H),
1.42(s,36H)。
In sum, the luminous organic material of present invention transmitting green glow is 4,7- bis- (3,5- di-tert-butyl-phenyl) -2,1,
3- diazosulfides, the green light material that the material is a kind of pure colourity, simple structure, fluorescence quantum yield is higher, dissolubility is good,
It is preferable green light luminescent material, has potential application in organic electroluminescence display field；
The preparation method operating process of the luminous organic material of present invention transmitting green glow is simple, and reaction condition is gentleer,
Product separating-purifying is simple, and yield is higher, and prepared green light material belongs to small molecule emitter material, has in luminescent device
Good application prospect.
The above embodiments are merely illustrative of the technical solutions of the present invention, rather than its limitations；Although with reference to the foregoing embodiments
The present invention has been described in detail, it will be understood by those within the art that：It still can be to foregoing each implementation
Technical scheme described in example is modified, or carries out equivalent to which part technical characteristic；And these modification or
Replace, do not make the spirit and scope of the essence disengaging various embodiments of the present invention technical scheme of appropriate technical solution.
Claims (8)
1. it is a kind of launch green glow luminous organic material, it is characterised in that：The luminous organic material is (3,5- bis- uncles of 4,7- bis-
Butyl phenyl) -2,1,3- diazosulfide, with the structure shown in formula (I)：
2. a kind of preparation method of luminous organic material as claimed in claim 1, it is characterised in that comprise the following steps：
S1, by 2,1,3- diazosulfide is added in the flask equipped with 40-60mlHBr solution, then to 25- is added dropwise in flask
35mlHBr solution, is stirred when being added dropwise, and 100-200 DEG C of backflow 4-8h is heated to after dripping, and cooling adds the sulfurous of saturation
Acid sodium solution, refilters, recrystallizes and obtain 4,7- bis- bromo- 2,1,3- diazosulfide；
S2, under nitrogen atmosphere, to equipped with toluene, K2CO34,7- bis- bromo- 2,1,3- benzo thiophene two are added in the flask of the aqueous solution
Azoles, 3,5- di-t-butyls phenyl boric acid, Cs2CO3, tetra-triphenylphosphine palladium, be heated to temperature for 100-150 DEG C, react 10-36h, it is cold
But, reactant mixture is obtained；
S3, by obtained in step S2 reactant mixture extract 2-4 times, then wash, dry, vacuum distillation, obtain crude product, then wash
De-, purification, obtains 4,7- bis- (3,5- di-tert-butyl-phenyl) -2,1,3- diazosulfide.
3. preparation method according to claim 2, it is characterised in that：4,7- bis- bromo- 2 described in step S2,1,3- benzo thiophene
The mol ratio of diazole and 3,5- di-t-butyl phenyl boric acid is 1：2-4.
4. preparation method according to claim 2, it is characterised in that：4,7- bis- bromo- 2 described in step S2,1,3- benzo thiophene
Diazole is 1 with the mol ratio of tetra-triphenylphosphine palladium：0.02-0.05.
5. preparation method according to claim 2, it is characterised in that：Temperature is heated to described in step S2 for 120-140 DEG C.
6. preparation method according to claim 2, it is characterised in that：Reaction time described in step S2 is 20-30h.
7. preparation method according to claim 2, it is characterised in that：Cooled down described in step S1, step S2 and be cooled to room
Temperature.
8. preparation method according to claim 2, it is characterised in that：The step S3 uses obtained reactant mixture
CH2Cl2Extraction three times, the crude product obtained after organic layer salt water washing, then crude product dichloromethane and petroleum ether are made
It is eluent, then carries out silica gel column chromatography purification, you can.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710044923.0A CN106867518A (en) | 2017-01-21 | 2017-01-21 | A kind of luminous organic material for launching green glow and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710044923.0A CN106867518A (en) | 2017-01-21 | 2017-01-21 | A kind of luminous organic material for launching green glow and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106867518A true CN106867518A (en) | 2017-06-20 |
Family
ID=59159102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710044923.0A Pending CN106867518A (en) | 2017-01-21 | 2017-01-21 | A kind of luminous organic material for launching green glow and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106867518A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101392174A (en) * | 2008-10-27 | 2009-03-25 | 华南理工大学 | Soluble electro-green light organic molecule glass material and preparation method and use thereof |
| CN101407717A (en) * | 2008-11-21 | 2009-04-15 | 吉林大学 | High efficient green electroluminescent material for processing solution in diazosulfide luminescent centre |
| JP2016025108A (en) * | 2014-07-16 | 2016-02-08 | 日東電工株式会社 | Wavelength conversion type sealing layer and solar battery module using the same |
-
2017
- 2017-01-21 CN CN201710044923.0A patent/CN106867518A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101392174A (en) * | 2008-10-27 | 2009-03-25 | 华南理工大学 | Soluble electro-green light organic molecule glass material and preparation method and use thereof |
| CN101407717A (en) * | 2008-11-21 | 2009-04-15 | 吉林大学 | High efficient green electroluminescent material for processing solution in diazosulfide luminescent centre |
| JP2016025108A (en) * | 2014-07-16 | 2016-02-08 | 日東電工株式会社 | Wavelength conversion type sealing layer and solar battery module using the same |
Non-Patent Citations (1)
| Title |
|---|
| KHALID M. OMER ET AL.: "Green Electrogenerated Chemiluminescence of Highly Fluorescent Benzothiadiazole and Fluorene Derivatives", 《J. AM. CHEM. SOC.》 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103194215B (en) | Preparation method of aggregation-induced emission molecule | |
| CN104326980B (en) | Based on 4,4 '-Lian two fluorene structured 9, the material of main part that 9 '-position connects and application thereof | |
| CN103664644A (en) | Organic semiconductor material containing aniline and preparation method thereof, and organic electroluminescence device | |
| CN106566533A (en) | Condensed ring oxidized thiophene-based organic luminescent material, and preparation method and application thereof | |
| CN104592194A (en) | Thianthrene oxide-aromatic amine organic luminescent small molecule as well as preparation and application thereof | |
| CN108774515A (en) | A kind of organic light emission combined material and its organic luminescent device | |
| CN106543123A (en) | A kind of connection anthracene compound and preparation method thereof and organic luminescent device | |
| CN109651423A (en) | A kind of dibenzo-heterocyclic compound and its preparation method and application | |
| CN106867520B (en) | Based on heteroaromatic simultaneously -2-S, the bipolarity small molecule emitter material and its preparation method of S- dioxydibenze bithiophene unit and application | |
| CN104311588B (en) | Aggregation-induced emission molecule based on silicon fluorene and its preparation method and application | |
| CN103073534A (en) | Organic semiconductor material, and preparation method and application thereof | |
| CN108822020A (en) | A kind of benzidine derivative and its organic electroluminescence device | |
| CN105503736B (en) | N-type compound and preparation and application of the one kind containing naphthalene [1,2] and imidazoles | |
| CN109020901A (en) | A kind of preparation of aromatic amine derivatives and its organic electroluminescence device | |
| CN109755415A (en) | The device of bipolar materials containing 4,6- diphenyl sulphone (DPS) dibenzofurans | |
| CN102050798B (en) | 2-(2'-hydroxylphenyl)-benzothiazole derivative luminescent materials | |
| CN106893578A (en) | A kind of bipolarity small molecule emitter material for being based on 3,7 naphtho- sulphur dibenzofuran units and preparation method and application | |
| CN103288811A (en) | Organic semiconductor material containing dibenzothiophene sulfone, preparation method of organic semiconductor material and organic electroluminescent device | |
| CN106867518A (en) | A kind of luminous organic material for launching green glow and preparation method thereof | |
| CN102850320B (en) | Compound containing dibenzothiophene sulfone and preparation method and application thereof | |
| CN107759624A (en) | New asymmetric aryl boron organic photoelectric functional material and preparation method and application | |
| CN107814726A (en) | A kind of organic compound containing fluorenes and its organic luminescent device | |
| CN107652286A (en) | A kind of derivative of tri-arylamine group and its organic luminescent device | |
| CN107235858A (en) | A kind of electroluminescent organic material and its organic luminescent device with electric transmission effect | |
| CN103588726A (en) | Spirobifluorene olefine organic electroluminescent material and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20170620 |
|
| RJ01 | Rejection of invention patent application after publication |