CN105777620A - Fluorenone pyridine green fluorescent material - Google Patents
Fluorenone pyridine green fluorescent material Download PDFInfo
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- CN105777620A CN105777620A CN201610285864.1A CN201610285864A CN105777620A CN 105777620 A CN105777620 A CN 105777620A CN 201610285864 A CN201610285864 A CN 201610285864A CN 105777620 A CN105777620 A CN 105777620A
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- fluorenone
- fluorescent material
- pyridine
- green fluorescent
- fluorenone pyridine
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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Abstract
The invention discloses a fluorenone pyridine green fluorescent material. The fluorenone pyridine green fluorescent material is characterized in that the fluorenone pyridine green fluorescent material is a fluorenone derivative with conjugate pyridine groups, and a molecular formula of the fluorenone pyridine green fluorescent material is C23H14N2O. The fluorenone pyridine green fluorescent material has the advantages that 2, 7-diiodo-9-fluorenone and 4-pyridine boric acid are synthesized by means of coupling reaction to obtain the fluorenone pyridine green fluorescent material, synthesis steps are simple, and the yield can reach 70%-90%; pyridyl is led into fluorenone pyridine, so that the photoelectric activity, namely, the luminous efficiency, of the fluorenone pyridine green fluorescent material can be greatly improved, and the fluorenone pyridine green fluorescent material which is used as an organic small-molecule fluorescent material has a potential application prospect in the field of organic light emitting devices and the like.
Description
Technical field
The invention belongs to technical field of material chemistry, be specifically related to a kind of Fluorenone pyridine green fluorescent material.
Background technology
Fluorescence usually occurs in the molecule with rigid plane and pi-electron conjugated system, and the size of intramolecular conjugated degree is
The major influence factors of material fluorescence property, therefore improves pi-electron conjugated degree in molecule, can be effectively improved molecular fluorescence and send out
Light efficiency.Fluorenes and Fluorenone class have rigid plane biphenyl structural, and intramolecular contains bigger conjugated system, and Fluorenone class material has
Having higher heat stability, the fluorescence quantum efficiency of solid film is higher, and band-gap energy is wider, is the important phosphor of a class
Material, more crucial is that compound of fluorene class is prone to carry out structural modification.But it is because fluorenes and the impact of this body structure of Fluorenone, easily
Form excimer and produce longwave transmissions, the colourity of overall emission light and the stability of color can be affected in the devices.
For improving the comprehensive luminescent properties of this kind of material, all kinds of research worker have carried out extensive work.
Common fluorenes class luminescent material based on polyfluorene (PFO) class, rigid plane that polyfluorene molecule is good and higher conjugation
Degree, has obtained the favor of many experts and scholars.The method generally used is to modify on 9 carbon of fluorenes, improves
Polyfluorene dissolving in organic solvent, is made material embody better performance after processing film forming, is regulated by steric hindrance simultaneously
The aggregated structure of material, keeps the stable crystal form of polyfluorene within the scope of certain temperature, improves the luminous efficiency of material.But
The structure of small molecule emitter material is easily adjusted, and can introduce various group to change the conjugated degree of molecule, improves performance.
For electroluminescent little molecule, there is chemical modification strong, it is easy to purify.By changing the chemical constitution of micromolecular compound,
We can change the emission wavelength of material.The present invention provides a kind of luminous organic material based on Fluorenone, by introducing pyridine
Group, improves the luminous efficiency of material, improves the performance of material.
Summary of the invention
The technical problem to be solved is for prior art, it is provided that a kind of Fluorenone pyridine green fluorescent material.
The present invention solves the technical scheme that above-mentioned technical problem used: a kind of Fluorenone pyridine green fluorescent material, and i.e. 2,7-
Two (4-pyridine radicals)-9-Fluorenone (is called for short Fluorenone pyridine), and its molecular formula is C23H14N2O, structural formula is:
Preferably, this fluorescent material has the specific electronic energy level structure being conjugated delocalization, and maximum emission peak (swashs at 506nm
Send out wavelength 339nm).
The preparation method of above-mentioned Fluorenone pyridine green fluorescent material, comprises the following steps:
1) by 2, the iodo-9-Fluorenone of 7-bis-, 4-pyridine boronic acid, sodium carbonate, acid chloride, in molar ratio 1:2～3:10:0.05
Ratio is mixed in reaction unit, and then by N, it is anti-that the ratio of N '-dimethyl Methanamide and water 10:1 by volume is mixed in this
Answer in device；
2) this reaction unit is reacted 12～24h in 90～150 DEG C；
3) after reaction terminates, extract with dichloromethane, separatory, merge organic facies, then by the saturated food of this organic facies
Saline washs three times, is dried with anhydrous sodium sulfate afterwards, filters；
4) organic solvent removed in filtrate by Rotary Evaporators i.e. obtains pressed powder, then using ethyl acetate as
Eluent uses column chromatographic isolation and purification, finally removes ethyl acetate, and obtained pressed powder is described Fluorenone
Pyridine green fluorescent material.
Preferably, the described material participating in reaction is chemical pure.
Fluorenone and derivant thereof are the luminous organic materials of a class function admirable, and Fluorenone molecule has the structural motif of rigidity conjugation,
Carbonyl on its 9 has stronger polarity, so that producing dipole effect between group；By coupling reaction at Fluorenone
2,7 upper introducings have the pyridine groups being conjugated big π key, make compound be provided with the specific electronic energy level structure being conjugated delocalization,
So that this compound has the fluorescent emission performance of uniqueness, obtain a kind of Fluorenone pyridine chemical combination with green fluorescence performance
Thing, the carbonyl and 2 of this compound 9, the pyridine radicals of 7 makes the electron delocalization of compound higher, thus improves compound
Luminous efficiency, be a kind of potential luminous organic material.
Accompanying drawing explanation
Fig. 1 is the fluorescence spectrum figure of the Fluorenone pyridine fluorescent material of the present invention.
Detailed description of the invention
Below in conjunction with accompanying drawing embodiment, the present invention is described in further detail.
Embodiment 1:
Take 2,7-bis-iodo-9-Fluorenone 3.0mmol, 4-pyridine boronic acid 6mmol, sodium carbonate 30mmol, acid chloride 0.15mmol
It is placed in the reaction unit of 150mL, and adds DMF 50mL and water 5mL；This reaction unit is reacted at 150 DEG C
12h；React complete, separatory after the cooling of question response liquid, use dichloromethane aqueous phase extracted, and merge organic facies, then will
This organic facies saturated aqueous common salt washs 3 times, is dried with anhydrous sodium sulfate afterwards, filters；Remove with Rotary Evaporators
Organic solvent in filtrate, obtains pressed powder, then uses column chromatographic isolation and purification using ethyl acetate as eluent,
Finally it is spin-dried for ethyl acetate, i.e. obtains described Fluorenone pyridine green fluorescent material.
Embodiment 2:
Take 2,7-bis-iodo-9-Fluorenone 3.0mmol, 4-pyridine boronic acid 9mmol, sodium carbonate 30mmol, acid chloride 0.15mmol
It is placed in the reaction unit of 150mL, and adds DMF 50mL and water 5mL；This reaction unit is reacted at 90 DEG C
24h；React complete, separatory after the cooling of question response liquid, use dichloromethane aqueous phase extracted, and merge organic facies, then will
This organic facies saturated aqueous common salt washs 3 times, is dried with anhydrous sodium sulfate afterwards, filters；Remove with Rotary Evaporators
Organic solvent in filtrate, obtains pressed powder, then uses column chromatographic isolation and purification using ethyl acetate as eluent,
Finally it is spin-dried for ethyl acetate, i.e. obtains described Fluorenone pyridine green fluorescent material.
Embodiment 3:
Take 2,7-bis-iodo-9-Fluorenone 3.0mmol, 4-pyridine boronic acid 7mmol, sodium carbonate 30mmol, acid chloride 0.15mmol
It is placed in the reaction unit of 150mL, and adds DMF 50mL and water 5mL；This reaction unit is reacted at 120 DEG C
18h；React complete, separatory after the cooling of question response liquid, use dichloromethane aqueous phase extracted, and merge organic facies, then will
This organic facies saturated aqueous common salt washs 3 times, is dried with anhydrous sodium sulfate afterwards, filters；Remove with Rotary Evaporators
Organic solvent in filtrate, obtains pressed powder, then uses column chromatographic isolation and purification using ethyl acetate as eluent,
Finally it is spin-dried for ethyl acetate, i.e. obtains described Fluorenone pyridine green fluorescent material.
The Fluorenone pyridine green fluorescent material prepared in above-described embodiment is pulverulent solids, through nucleus magnetic hydrogen spectrum, infrared, ultraviolet,
It is C that mass spectrum, elementary analysis etc. measure its molecular formula23H14N2O。
Fluorescence property test is carried out, its fluorescence spectrum figure such as figure after obtained Fluorenone pyridine green fluorescent material natural air drying
Shown in 1.
Claims (2)
1. a Fluorenone pyridine green fluorescent material, it is characterised in that this fluorescent material be a kind of containing conjugation pyridine groups and
The organic compound of ketone group, its entitled 2,7-bis-(4-pyridine radicals)-9-Fluorenone (be called for short Fluorenone pyridine), its molecular formula is
C23H14N2O, structural formula is:
Fluorenone pyridine green fluorescent material the most according to claim 1, it is characterised in that this fluorescent material has specific
The electronic energy level structure of conjugation delocalization, maximum emission peak is 506nm (excitation wavelength is 339nm).
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| CN201610285864.1A CN105777620B (en) | 2016-04-29 | 2016-04-29 | A kind of Fluorenone pyridine green fluorescent material |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106188154A (en) * | 2016-07-26 | 2016-12-07 | 宁波大学 | A kind of ferra formed material and preparation method thereof |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6255449B1 (en) * | 1995-07-28 | 2001-07-03 | The Dow Chemical Company | Fluorene-containing polymers and compounds useful in the preparation thereof |
| US20020132134A1 (en) * | 2001-01-26 | 2002-09-19 | Xerox Corporation | Electroluminescent (EL) devices |
| EP1284258A2 (en) * | 2001-08-17 | 2003-02-19 | MERCK PATENT GmbH | Mono-, oligo- and polyalkylidenefluorenes and their use as charge transport materials |
| CN101928276A (en) * | 2010-07-15 | 2010-12-29 | 太原理工大学 | Method for synthesizing organic red light material |
| CN102838442A (en) * | 2012-08-09 | 2012-12-26 | 烟台万润精细化工股份有限公司 | 9-alkenylfluorene derivatives and application thereof |
| CN105503766A (en) * | 2015-12-18 | 2016-04-20 | 昆山国显光电有限公司 | Thermal activation delayed fluorescent material and organic electroluminescent device |
-
2016
- 2016-04-29 CN CN201610285864.1A patent/CN105777620B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6255449B1 (en) * | 1995-07-28 | 2001-07-03 | The Dow Chemical Company | Fluorene-containing polymers and compounds useful in the preparation thereof |
| US20020132134A1 (en) * | 2001-01-26 | 2002-09-19 | Xerox Corporation | Electroluminescent (EL) devices |
| EP1284258A2 (en) * | 2001-08-17 | 2003-02-19 | MERCK PATENT GmbH | Mono-, oligo- and polyalkylidenefluorenes and their use as charge transport materials |
| CN101928276A (en) * | 2010-07-15 | 2010-12-29 | 太原理工大学 | Method for synthesizing organic red light material |
| CN102838442A (en) * | 2012-08-09 | 2012-12-26 | 烟台万润精细化工股份有限公司 | 9-alkenylfluorene derivatives and application thereof |
| CN105503766A (en) * | 2015-12-18 | 2016-04-20 | 昆山国显光电有限公司 | Thermal activation delayed fluorescent material and organic electroluminescent device |
Non-Patent Citations (3)
| Title |
|---|
| NIU ZHIGANG ET AL.: "Syntheses, Electrochemical Behaviors, Spectral Properties and DFT Calculations of Two 1,3-Dithiole Derivatives.", 《CHEM. RES. CHIN. UNIV.》 * |
| 刘志鹏: "芴类有机发光材料的合成及性能表征", 《宁波大学硕士学位论文》 * |
| 杨伟等: "吡啶 芴类电荧光聚合物的光谱特性", 《高分子学报》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106188154A (en) * | 2016-07-26 | 2016-12-07 | 宁波大学 | A kind of ferra formed material and preparation method thereof |
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Effective date of registration: 20201127 Address after: Room 1,020, Nanxun Science and Technology Pioneering Park, No. 666 Chaoyang Road, Nanxun District, Huzhou City, Zhejiang Province, 313000 Patentee after: Huzhou You Yan Intellectual Property Service Co.,Ltd. Address before: 315211 Zhejiang Province, Ningbo Jiangbei District Fenghua Road No. 818 Patentee before: Ningbo University |
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Effective date of registration: 20211111 Address after: 256600 No. 1, Gaosi Road, high tech Industrial Development Zone, Binzhou City, Shandong Province Patentee after: Binzhou Kechuang Incubator Co., Ltd Address before: 313000 room 1020, first floor, Nanxun science and technology entrepreneurship Park, No. 666, Chaoyang Road, Nanxun Town, Nanxun District, Huzhou City, Zhejiang Province Patentee before: Huzhou Youyan Intellectual Property Service Co., Ltd |