CN106398682A - Tripolyphosphazene-nucleated star-shaped organic blue-light material and preparation method therefor - Google Patents
Tripolyphosphazene-nucleated star-shaped organic blue-light material and preparation method therefor Download PDFInfo
- Publication number
- CN106398682A CN106398682A CN201610162040.5A CN201610162040A CN106398682A CN 106398682 A CN106398682 A CN 106398682A CN 201610162040 A CN201610162040 A CN 201610162040A CN 106398682 A CN106398682 A CN 106398682A
- Authority
- CN
- China
- Prior art keywords
- tripolyphosphazene
- anthracene
- organic
- star
- reaction
- 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
- 239000000463 material Substances 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 230000005669 field effect Effects 0.000 claims abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
- 239000007787 solid Substances 0.000 claims description 13
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000013067 intermediate product Substances 0.000 claims description 8
- 239000000725 suspension Substances 0.000 claims description 8
- 150000001454 anthracenes Chemical class 0.000 claims description 7
- 239000011368 organic material Substances 0.000 claims description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 238000005352 clarification Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- 235000002639 sodium chloride Nutrition 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- ORPDTKXFAPFHPD-UHFFFAOYSA-N anthracene;boric acid Chemical compound OB(O)O.C1=CC=CC2=CC3=CC=CC=C3C=C21 ORPDTKXFAPFHPD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000012141 concentrate Substances 0.000 claims description 2
- 239000000284 extract Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- -1 stopped reaction Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000007039 two-step reaction Methods 0.000 claims description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 abstract description 12
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000004132 cross linking Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 2
- OUCSIUCEQVCDEL-UHFFFAOYSA-N 2,3,4-tribromophenol Chemical compound OC1=CC=C(Br)C(Br)=C1Br OUCSIUCEQVCDEL-UHFFFAOYSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- ZSTLPJLUQNQBDQ-UHFFFAOYSA-N azanylidyne(dihydroxy)-$l^{5}-phosphane Chemical group OP(O)#N ZSTLPJLUQNQBDQ-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/65812—Cyclic phosphazenes [P=N-]n, n>=3
- C07F9/65815—Cyclic phosphazenes [P=N-]n, n>=3 n = 3
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- 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
- C09K2211/107—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with other heteroatoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to an organic luminescent material. A structural general formula of the organic luminescent material is represented by a formula shown in the description, wherein n is 1 or 2, and R is a substituent. A star-shaped molecular structure is formed through taking tripolyphosphazene as a nucleus and cross-linking a luminophore, i.e., anthracene to the nucleus by a chemical bond. The compound has both the thermal stability of the tripolyphosphazene and the blue-light emitting property of the anthracene, and comprehensive properties of the material are improved remarkably due to a special spatial clustering mode of the luminophore after the tripolyphosphazene and the anthracene are combined, so that the material is a novel organic luminescent material and can be used for manufacturing photoelectric conversion devices such as large-area colored flexible display screens and field-effect diodes.
Description
Technical field
The present invention relates to new chemical materialses technical field is and in particular to a kind of luminous organic material and preparation method.
Background technology
Luminous organic material low cost can prepare large-area flexible device.Organic Light Emitting Diode (OLED) has the features such as startup voltage is low, brightness is high, fast response time, luminous efficiency are high, can apply to the fields such as large-area colour flexible display screen of new generation and solid state lighting.
Luminous organic material is the key factor of organic photoelectric switching device and its industry development.Have been developed over some OLED luminescent materials at present, be concentrated mainly on triaryl amine system, anthracene derivative, carbazole derivates, some classical chemical combination objects systems such as rare earth metal complex.But, current material also has the problem of many application aspect, such as service life, luminosity, luminous efficiency etc., and the luminescent material of exploitation high comprehensive performance is an important direction of scientific rersearch.
In Panchromatic great-arear field of flexible display, organic red light and green light material species are more, and organic blue light material species is fewer.At present, organic blue light material, in terms of service life, luminous efficiency and spectral purity, also has larger gap, exploitation with HONGGUANG and green organic luminescenceNewOrganic blue light material is the driving source promoting correlation technique constantly to develop and apply.
Content of the invention
It is an object of the invention to provide a kind of tripolyphosphazene of high comprehensive performance is organic blue light material of core.
Another object of the present invention is to provide a kind of simple method preparing organic blue light material that tripolyphosphazene is core.
For realizing first purpose, technical scheme is as follows：
The invention provides a kind of with tripolyphosphazene as core, the hyperbranched star molecular structure as luminophore for the anthracene nucleus, it is bonded with the chemistry of luminophore that ring three phosphonitrile core to be realized with phenyl ring or oligomerization benzene in centre, it is characterized in that, this tripolyphosphazene is that the luminous organic material formula of core is：
Wherein n=1,2；Anthracene nucleus passes through 9 carbon atoms and phenyl ring bridging, and link position can be para-position, meta or the ortho position of phenyl ring；R is any possible substituent group on anthracene nucleus, can be electrophilic group, electron-donating group, aromatic group or alkyl etc..
For realizing second purpose, present invention also offers having above-mentionedNewThe preparation method of the luminous organic material of structure, feature is including two-step reaction：
Step (1):By potassium carbonate (K2CO3), bromophenol, oxolane (THF) mix according to a certain percentage, stir, obtaining white suspension, for a period of time, suspension becomes clarification to heated constant temperature, is subsequently adding hexachlorocyclotriph,sphazene,, until white solid in reaction a period of time under uniform temperature and stirring condition；Stopped reaction, extracts filtrate by reacting liquid filtering, with saturated aqueous common salt, to organic layer through drying, filter, concentrate, precipitation, washing, be dried after intermediate product；
Step (2):By the intermediate product prepared by above-mentioned steps (1), K2CO3The mix homogeneously such as solution, anthracene boric acid, tetra-triphenylphosphine palladium, THF, under nitrogen protection, reaction a period of time under uniform temperature and stirring condition, until reactant liquor is changed into brown from light yellow；Stopped reaction, filter, precipitation, washing, dry, refined, obtain pulverulent solids.
With respect to prior art, the invention has the advantages that：
1. the present invention devises one kindNewOrganic blue light material is with tripolyphosphazene as core, the hyperbranched star molecule as luminophore for the anthracene nucleus.
2. the good feature of tripolyphosphazene heat stability is combined by the present invention with the high blue light purity of anthracene and high-luminous-efficiency feature, to realizeNewOrganic blue light material resultant performance enhancements, heat stability and blue light-emitting aspect of performance advantage are integrated.
3. the tripolyphosphazene that the present invention provides is that the preparation method of organic blue light material of core is simple, easily realizes industrialized production.
Brief description
Figure 1For embodiment 1 gained tripolyphosphazene be core the organic blue light material of star uv-vis spectra (CH2Cl2Dissolving)；
Figure 2For embodiment 1 gained tripolyphosphazene be core the organic blue light material of star fluorescence emission spectrumFigure (Excitation wavelength is 367nm, slit 5nm, CH2Cl2Dissolving)；
Figure 3For embodiment 1 gained tripolyphosphazene be core the organic blue light material of star thermogravimetric analysiss spectrumFigure；
Figure 4For embodiment 2 gained tripolyphosphazene be core the organic blue light material of star uv-vis spectra (CH2Cl2Dissolving)；
Figure 5For embodiment 2 gained tripolyphosphazene be core the organic blue light material of star fluorescence emission spectrumFigure (Excitation wavelength is 367nm, slit 5nm, CH2Cl2Dissolving)；
Figure 6For embodiment 2 gained tripolyphosphazene be core the organic blue light material of star thermogravimetric analysiss spectrumFigure.
Specific embodiment
The invention will be further described below：
Case study on implementation
Embodiment 1：The synthesis of compound 001, concrete preparation manipulation step is as follows：
Step (1) is by 4.80g K2CO3(34.8mmol), the THF solution of 5.00g p bromophenol (29.0mmol) and 50mL drying is added sequentially to two mouthfuls of flasks and forms white suspension, 70 DEG C of constant temperature stir 1 hour, when suspension becomes clarification, instill the THF weak solution of 1.00g hexachlorocyclotriph,sphazene (2.90mmol),, white solid stopped reaction in 70 DEG C of isothermal reaction 48h.By reacting liquid filtering, filter solid, take filtrate, then use saturation NaCl solution to extract 3 times, use anhydrous MgSO4Organic layer is dried, filters revolving, wash 2 times, filtration drying with methanol, obtain intermediate product 3.14g, yield is 92.7%.
The above-mentioned intermediate product (1.00mmol) that 1.170g step (1) is prepared by step (2), 2M K2CO3Solution 5mL, the ethanol solution of the boric acid of anthracene containing 2.00g (9.00mmol), 0.310g tetra-triphenylphosphine palladium (0.27mol), 50mL THF is added in two-mouth bottle, and reactant liquor is in light yellow, and evacuation-inflated with nitrogen is continuously taken a breath 3 times.Under conditions of 90 DEG C of oil baths, continuous stirring 48h.When reactant liquor from light yellow be changed into brown when stopped reaction.Question response liquid filters after being cooled to room temperature, filtrate is poured in excessive methanol, light yellow solid, filters, and is dried, and obtains pulverulent solids, column chromatography for separation, and eluent is dichloromethane/petroleum ether, obtains target product 1.170g, and yield is 66.8%.Compound 001 structural formula is
Nuclear-magnetism is as follows with mass spectrometric data,1H NMR(400MHz,CDCl3) δ 8.43 (s, 6H), 7.97 (s, 12H), 7.66 (d, J=13.8Hz, 24H), 7.48 (s, 12H), 7.29 (d, J=21.7Hz, 12H), 7.20 6.80 (m, 12H).
MALDI-TOF-MS(m/z):1751.9
Embodiment 2：The synthesis of compound 002, concrete preparation manipulation step is as follows：
Step (1) is by 4.80g K2CO3(34.8mmol), the THF solution of 5.00g tribromphenol (29.0mmol) and 50mL drying is added sequentially to two mouthfuls of flasks and forms white suspension, 70 DEG C of constant temperature stir 1 hour, when suspension becomes clarification, the THF weak solution of 1.00g hexachlorocyclotriph,sphazene (2.90mmol) is added in clear liquor,, stopped reaction during white solid in 70 DEG C of isothermal reaction 48h.By reacting liquid filtering, filter solid, take filtrate, then use saturation NaCl solution to extract 3 times, use anhydrous MgSO4Organic layer is dried, filters revolving, wash 2 times, filtration drying with methanol, obtain 3.30g intermediate product 2, yield is 96.0%.
The above-mentioned intermediate product (1.00mmol) that 1.170g step (1) is prepared by step (2), 2M K2CO3Solution 5mL, the ethanol solution of the boric acid of anthracene containing 2.00g (9.00mmol), 0.310g tetra-triphenylphosphine palladium (0.27mol), 50mL THF is added in two-mouth bottle, and reactant liquor is in light yellow, and evacuation-inflated with nitrogen is continuously taken a breath 3 times.Under conditions of 90 DEG C of oil baths, continuous stirring 48h.When reactant liquor from light yellow be changed into brown when stopped reaction.Question response liquid filters after being cooled to room temperature, filtrate is poured in excessive methanol, light yellow solid, filters, and is dried, and obtains pulverulent solids, column chromatography for separation, and eluent is dichloromethane/petroleum ether, obtains target product 1.318g, and yield is 75.2%.Compound 002 structural formula is
Nuclear magnetic data is as follows,1H NMR(400MHz,CDCl3) δ 8.33 (s, 6H), 7.86 (d, J=7.6Hz, 12H), 7.44 (d, J=8.0Hz, 12H), 7.23 (d, J=27.2Hz, 12H), 6.96 (dd, J=37.1,30.4Hz, 36H).
MALDI-TOF-MS(m/z):1751.5
Finally illustrate is, above example is only in order to illustrate technical scheme and unrestricted, although being described in detail to the present invention with reference to preferred embodiment, it will be understood by those within the art that, technical scheme can be modified or equivalent, objective without deviating from technical solution of the present invention and scope, it all should be covered the present invention'sClaimIn.
Claims (3)
1. a kind of organic blue light material with tripolyphosphazene as core is it is characterised in that the general structure of the organic blue-light emitting material of the star as core for this tripolyphosphazene is：
Wherein n=1,2；Anthracene nucleus passes through 9 carbon atoms and phenyl ring bridging, and link position can be para-position, meta or the ortho position of phenyl ring；R is any possible substituent group on anthracene nucleus, can be electrophilic group, electron-donating group, aromatic group or alkyl etc..
2.According to claimThe preparation method of the luminous organic material described in 1, its feature includes preparing by two-step reaction：
Step (1):By potassium carbonate (K2CO3), bromophenol, oxolane (THF) mix according to a certain percentage, stir, obtaining white suspension, heated constant temperature is for a period of time, suspension becomes clarification, it is subsequently adding hexachlorocyclotriph,sphazene, reaction a period of time under uniform temperature and stirring condition, until white solid, stopped reaction, extract filtrate by reacting liquid filtering, with saturated aqueous common salt, to organic layer through drying, filter, concentrate, precipitation, washing, be dried after intermediate product；
Step (2):By the intermediate product prepared by above-mentioned steps (1), K2CO3The mix homogeneously such as solution, anthracene boric acid, tetra-triphenylphosphine palladium, THF, under nitrogen protection, reaction a period of time under uniform temperature and stirring condition, until reactant liquor is changed into brown from light yellow；Stopped reaction, filter, precipitation, washing, dry, refined, obtain pulverulent solids.
3. one kind is required application in organic photoelectric switching device (electroluminescent, photovoltaic generation, colored display, field-effect diode etc.) and other possible fields for any one luminous organic material as described in 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610162040.5A CN106398682A (en) | 2016-03-21 | 2016-03-21 | Tripolyphosphazene-nucleated star-shaped organic blue-light material and preparation method therefor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610162040.5A CN106398682A (en) | 2016-03-21 | 2016-03-21 | Tripolyphosphazene-nucleated star-shaped organic blue-light material and preparation method therefor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106398682A true CN106398682A (en) | 2017-02-15 |
Family
ID=58007108
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610162040.5A Pending CN106398682A (en) | 2016-03-21 | 2016-03-21 | Tripolyphosphazene-nucleated star-shaped organic blue-light material and preparation method therefor |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106398682A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110746462A (en) * | 2019-10-25 | 2020-02-04 | 北京理工大学 | Efficient synthesis method of dendritic cyclotriphosphazene compound |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101467280A (en) * | 2006-05-15 | 2009-06-24 | 日东电工株式会社 | Light emitting devices and compositions |
| CN105027314A (en) * | 2013-03-05 | 2015-11-04 | 国立大学法人九州大学 | Charge transport material, host material, thin film and organic light emitting element |
| CN105062469A (en) * | 2015-08-26 | 2015-11-18 | 重庆理工大学 | Six-nuclear cyclotriphosphazene terbium complex light-emitting material and preparation method thereof |
-
2016
- 2016-03-21 CN CN201610162040.5A patent/CN106398682A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101467280A (en) * | 2006-05-15 | 2009-06-24 | 日东电工株式会社 | Light emitting devices and compositions |
| CN105027314A (en) * | 2013-03-05 | 2015-11-04 | 国立大学法人九州大学 | Charge transport material, host material, thin film and organic light emitting element |
| CN105062469A (en) * | 2015-08-26 | 2015-11-18 | 重庆理工大学 | Six-nuclear cyclotriphosphazene terbium complex light-emitting material and preparation method thereof |
Non-Patent Citations (3)
| Title |
|---|
| SUNDARRAJ SUDHAKAR 等: "Nanocomposite Dendrimers Based on Cyclic Phosphazene Cores: Amorphous Materials for Electroluminescent Devices", 《MACROMOL. RAPID COMMUN.》 * |
| T. MA 等: "Design and Synthesis of New Cyclic Phosphazene Based Blue Light- Emitting Dendrimers", 《INTERNATIONAL CONFERENCE ON INDUSTRIAL TECHNOLOGY AND MANAGEMENT SCIENCE》 * |
| 马涛: "三聚磷腈为核的超支化蓝光材料的设计与合成", 《中国优秀硕士学位论文全文数据库 信息工程I辑》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110746462A (en) * | 2019-10-25 | 2020-02-04 | 北京理工大学 | Efficient synthesis method of dendritic cyclotriphosphazene compound |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110790782A (en) | Dark blue organic luminescent material and preparation method and application thereof | |
| CN102229623B (en) | Spirofluorene xanthene phosphine oxide electro-phosphorescent main materials and synthesis and application methods thereof | |
| CN103193733B (en) | 2,7-di-(N-phenothiazinyl)fluorenone and preparation method thereof | |
| CN108084150B (en) | Organic supramolecular white light emitting material and preparation method thereof and OLED device | |
| CN109928936B (en) | Organic electroluminescent compounds and use thereof | |
| CN103242298A (en) | 1,2,4-triazole derivative, preparation method and application thereof and organic electroluminescent device | |
| CN104629721B (en) | Organic luminescent material with excellent performance and preparation method thereof | |
| Zhao et al. | Solution-processible 1, 3, 4-oxadiazole/spiro [fluorene-9, 9′-xanthene] hybrid as efficient host for green thermally activated delayed fluorescence devices | |
| CN113402561A (en) | High-color-purity platinum (II) complex luminescent material based on spirofluorene structure and application thereof | |
| CN111925392B (en) | Copper compound with photoluminescence performance and preparation method thereof | |
| CN109593049B (en) | Binaphthol solid fluorescent material | |
| CN106398682A (en) | Tripolyphosphazene-nucleated star-shaped organic blue-light material and preparation method therefor | |
| Hsu et al. | Fluorescent oligomers of dibenzothiophene-S, S-dioxide derivatives: the interplay of crystal conformations and photo-physical properties | |
| CN103525401B (en) | Spirobifluorene derivative organic electroluminescence material as well as preparation method thereof | |
| CN103242358B (en) | Siliceous dianthranide derivative and its preparation method and application and organic electroluminescence device | |
| KR101570449B1 (en) | Novel BODIPY derivative for green organic light-emitting diode dopant and method for preparing the same | |
| CN115651029A (en) | Spirofluorene-biphenyl-azaacridine-based four-tooth cyclometalated platinum (II) complex phosphorescent light-emitting material and application thereof | |
| Zhang et al. | Synthesis of Fluorene‐Bridged Arylene Vinylene Fluorophores: Effects of End‐Capping Groups on the Optical Properties, Aggregation Induced Emission | |
| CN114437139A (en) | Luminescent material of tetradentate 6/5/6 cyclometalated platinum (II) complex based on azacarbazole-spirofluorene structure and application thereof | |
| CN113201022A (en) | Small conjugated phosphorescent metal iridium (III) complex with isomer and preparation method and application thereof | |
| CN106749076A (en) | O-hydroxy-phenyl azole derivative as organic blue light material application | |
| CN113583056A (en) | 6/5/6 tetradentate cyclometalated platinum or palladium complex luminescent material based on spirofluorene-spirofluorene structure and application thereof | |
| CN109456346B (en) | Boron-containing compound and preparation method and application thereof | |
| CN108558595B (en) | P-phenylene ethylene bridged trimer indene derivative and preparation method thereof | |
| CN104629719B (en) | Fluorene derivatives and applications thereof in electroluminescent devices |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20170215 |
|
| WD01 | Invention patent application deemed withdrawn after publication |