CN107746384A - A kind of purple fluorescence material crystals and preparation method based on trifluoromethyl - Google Patents
A kind of purple fluorescence material crystals and preparation method based on trifluoromethyl Download PDFInfo
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- CN107746384A CN107746384A CN201711128734.8A CN201711128734A CN107746384A CN 107746384 A CN107746384 A CN 107746384A CN 201711128734 A CN201711128734 A CN 201711128734A CN 107746384 A CN107746384 A CN 107746384A
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
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Abstract
The invention discloses a kind of purple fluorescence material crystals based on trifluoromethyl and preparation method thereof, the material is 9 [3,5 two (trifluoromethyl) phenyl] 9H carbazoles, shown in structure such as formula (I)：Crystallized by the mixed solvent of ethanol and dichloromethane, respectively obtain the white needle-like crystals of the material, the material mono-crystalline structures are rhombic system, crystallographic axisInterplanar angle α=90.00 °, β=90.00 °, γ=90.00 °.The purple fluorescence material crystals based on trifluoromethyl in the present invention, have preparation method simple, small in violet photoluminescence, singlet triplet difference, electroluminescent device luminescent layer can be used for as purple delayed fluorescence material.
Description
Technical field
The invention belongs to technical field of organic luminescence materials, and in particular to a kind of purple fluorescence material based on trifluoromethyl
Crystal and preparation method.
Background technology
Purple fluorescence material has boundless application prospect in fields such as FPD, information storages.
Compared with red, green and blue fluorescent material, purple fluorescence material is due to requiring MOLECULE DESIGN high, it is necessary to tight
Lattice control the conjugated degree of molecule.So far, purple fluorescence material category and few, the purple fluorescence material of a large amount of excellent performances
Material has to be designed and synthesis, the report about purple fluorescence material crystals even more rare.The purple fluorescence material reported at present
Mainly have diphenyl sulfone derivative (Ye J et al.Chemistry of Materials, 2013,25：2630-2637), anthracene spreads out
Biology (Hu J.-Y et al.Adv.Mater., 2014,24：2064-2071), phenanthro- imdazole derivatives (Gao Z et
Al.Chem.-Eur.J., 2013,19：2602-2605) etc..Example of the compound containing trifluoromethyl as purple fluorescence material
It is actually rare.It is well known that the electron withdraw group that trifluoromethyl is strong as one, is incorporated into molecule, molecule will not be increased
Conjugation, and electron-withdrawing power can be increased, it is advantageously implemented the fluorescent emission of short wavelength.
The content of the invention
An object of the present disclosure is to provide a kind of purple fluorescence for being based on 9- [3,5 two (trifluoromethyl) phenyl] -9H- carbazoles
Material crystals.
Second purpose of the invention is to provide the preparation method of the purple fluorescence material crystals.
In order to realize the first goal of the invention of the present invention, the present invention adopts the following technical scheme that：
A kind of purple fluorescence material crystals, the material are 9- [3,5 two (trifluoromethyl) phenyl] -9H- carbazoles, and structure is such as
Formula (I)
It is shown：
In order to realize the second goal of the invention of the present invention, the present invention adopts the following technical scheme that：
A kind of preparation method of purple fluorescence material crystals, is comprised the steps of：
With bromo- 3,5- bis- (trifluoromethyl) benzene of 1- for raw material, coughed up with carbazole, Anhydrous potassium carbonate, iodate Asia ketone, 1,10- phenanthrene
Quinoline monohydrate, DMF 1: 1~1.2: 1.5~2: 0.1~0.2: 0.1~0.2: 20~50 enter in molar ratio
Row is well mixed, by mixture 20~40h of back flow reaction under nitrogen protection.Reactant is by adding water quenching go out, extract, post layer
Analysis, and the elution for the petroleum ether for being 60-90 DEG C with boiling range, obtain 9- [3,5 two (trifluoromethyl) phenyl] -9H- carbazole solids；
By 9- [3,5 two (trifluoromethyl) phenyl] -9H- carbazole solids, with dichloromethane, ethanol in mass ratio 1: 40~80
: 40~80 carry out mixed dissolution, and room temperature solvent flashing obtains white needle-like crystals, and the white needle-like crystals are purple fluorescence
Material crystals.
Purple fluorescence material crystals mono-crystalline structures of the present invention based on trifluoromethyl are rhombic system, crystallographic axis Interplanar angle α=90.00 °, β=90.00 °, γ=
90.00 °, elementary cell volume (VElementary cell) beMolecular number (Z) in elementary cell is 8, and density (d) density is
1.533Mg/m3。
By above-mentioned material dissolution of crystals in dichloromethane solution (1g/100mL), then equably it is spin-coated on silicon chip,
50 DEG C of drying 30min, are made film.The fluorescence emission spectrum and fluorescent quantum of above-mentioned material film at room temperature are determined respectively
Efficiency, and fluorescence emission spectrum and phosphorescence emission spectra (μ s of time delay 100) in 77K.Purple fluorescence material crystals,
Fluorescence emission wavelengths during room temperature in the film are 387nm, fluorescent emission ripple when absolute fluorescence quantum efficiency is 0.22,77K
Long and phosphorescence start wavelength is respectively 392 and 416nm, and corresponding singlet energy level and triplet are respectively 3.18 Hes
2.98eV, singlet-triplet difference is 0.20eV.
Compared with prior art, the invention has the advantages that：
The present invention obtains purple fluorescence material crystals, and materials synthesis route is short, crystal preparation method simple possible, is easy to big
It is prepared by scale.The purple fluorescence material crystals of the present invention, emission wavelength is short, and singlet-triplet difference is small, can be used as purple
Delayed fluorescence material is used for electroluminescent device luminescent layer.
Brief description of the drawings
Fig. 1 is the mono-crystalline structures figure of material.
Fig. 2 is the structure cell accumulation graph of material monocrystalline.
Fig. 3 is material1H NMR spectras.
Embodiment
With reference to embodiments, the invention will be further described.Reagent used in the present invention is bought from traditional Chinese medicines company.
Proton nmr spectra (1H NMR) it is measured with Bruker (ARX-300) NMR, deuterated chloroform (CDCl3) make
Solvent, tetramethylsilane (TMS) are internal standard.Fluorescence emission spectrum, fluorescence quantum efficiency and phosphorescence emission spectra are to use Jobin
The FLUOROLOG-4 XRFs measure of Yvon companies, scanning wavelength 350~650nm of scope, spectrum when determining phosphorescent emissions
Postpone 100 μ s to eliminate fluorescence interference.Bruker D8 Venture X ray of the single crystal X-ray diffraction test in Germany's production
Carried out on diffractometer.
Specific reaction scheme is as follows：
Embodiment 1：The preparation of 9- [3,5 two (trifluoromethyl) phenyl] -9H- carbazoles
Add bromo- (trifluoromethyl) benzene of 3,5- bis- 2.91g (10mmol) of 1-, carbazole 1.80g (10.8mmol), cuprous iodide
0.19g (1mmol), Anhydrous potassium carbonate 2.72g (20mmol), 1,10- phenanthroline monohydrate 0.2g (1mmol) and N, N- diformazan
Base formamide 73g (1mol) is well mixed, under nitrogen protection back flow reaction 40h.Reaction solution is cooled to room temperature, pours into 100g water
Middle precipitation solid, by filter cake sand and pass through column chromatography after suction filtration, the petroleum ether for being 60-90 DEG C with boiling range elutes, and obtains white
Solid, yield 63.1%.1H NMR (300MHz, CDCl3)δ(ppm)：8.18 (d, J=7.8Hz, 2H), 8.11 (s, 2H), 7.99
(s, 1H), 7.50 (t, J=7.2Hz, 6.9Hz, 2H), 7.42-7.35 (m, 4H).1H NMR spectras are as shown in Figure 3.
Embodiment 2：The preparation of 9- [3,5 two (trifluoromethyl) phenyl] -9H- carbazoles
Add bromo- (trifluoromethyl) benzene of 3,5- bis- 2.91g (10mmol) of 1-, carbazole 1.67g (10mmol), cuprous iodide
0.39g (2mmol), Anhydrous potassium carbonate 2.04g (15mmol), 1,10- phenanthroline monohydrate 0.40g (2mmol) and N, N- bis-
NMF 36.5g (0.5mol) is well mixed, under nitrogen protection back flow reaction 20h.Reaction solution is cooled to room temperature, pours into
Separate out solid in 50g water, by filter cake sand and pass through column chromatography after suction filtration, the petroleum ether for being 60-90 DEG C with boiling range elutes, and obtains
White solid, yield 53.9%.1H NMR (300MHz, CDCl3)δ(ppm)：8.18 (d, J=7.8Hz, 2H), 8.11 (s, 2H),
7.99 (s, 1H), 7.50 (t, J=7.2Hz, 6.9Hz, 2H), 7.42-7.35 (m, 4H).1H NMR spectras are as shown in Figure 3.
Embodiment 3：The preparation of 9- [3,5 two (trifluoromethyl) phenyl] -9H- carbazoles
Add bromo- (trifluoromethyl) benzene of 3,5- bis- 2.91g (10mmol) of 1-, carbazole 2.0g (12mmol), cuprous iodide
0.19g (1mmol), Anhydrous potassium carbonate 2.72g (20mmol), 1,10- phenanthroline monohydrate 0.20g (1mmol) and N, N- bis-
NMF 73g (1mol) is well mixed, under nitrogen protection back flow reaction 20h.Reaction solution is cooled to room temperature, pours into 100g
Separate out solid in water, by filter cake sand and pass through column chromatography after suction filtration, the petroleum ether for being 60-90 DEG C with boiling range elutes, and obtains white
Color solid, yield 64.2%.1H NMR (300MHz, CDCl3)δ(ppm)：8.18 (d, J=7.8Hz, 2H), 8.11 (s, 2H),
7.99 (s, 1H), 7.50 (t, J=7.2Hz, 6.9Hz, 2H), 7.42-7.35 (m, 4H).1H NMR spectras are as shown in Figure 3.
Embodiment 4：The preparation of 9- [3,5 two (trifluoromethyl) phenyl] -9H- carbazole crystal
By 9- [3,5 two (trifluoromethyl) phenyl] -9H- carbazole solids, with dichloromethane, ethanol in mass ratio 1: 40: 40
Mixed dissolution is carried out, room temperature solvent flashing, obtains white needle-like crystals.Using X-ray diffractometer, white needle-like crystals are carried out
Single crystal X-ray diffraction test, as a result for：Crystallographic system is rhombic system, space group Pbca, crystallographic axis Interplanar angle α=90.00 °, β=90.00 °, γ=90.00 °, elementary cell
Volume (VElementary cell) beMolecular number (Z) in elementary cell is 8, and density (d) density is 1.533Mg/m3.Monocrystalline
Structure and accumulation graph are as depicted in figs. 1 and 2.
Embodiment 5：The preparation of 9- [3,5 two (trifluoromethyl) phenyl] -9H- carbazole crystal
By 9- [3,5 two (trifluoromethyl) phenyl] -9H- carbazole solids, with dichloromethane, ethanol in mass ratio 1: 80: 80
Mixed dissolution is carried out, room temperature solvent flashing, obtains white needle-like crystals.Crystallographic system is rhombic system, space group Pbca, crystallographic axisInterplanar angle α=90.00 °, β=90.00 °, γ=
90.00 °, elementary cell volume (VElementary cell) beMolecular number (Z) in elementary cell is 8, and density (d) density is
1.533Mg/m3.Mono-crystalline structures and accumulation graph are as depicted in figs. 1 and 2.
Embodiment 6：The photophysical property of 9- [3,5 two (trifluoromethyl) phenyl] -9H- carbazole crystal
By above-mentioned material dissolution of crystals in dichloromethane solution (1g/100mL), then equably it is spin-coated on silicon chip,
50 DEG C of drying 30min, are made film.The fluorescence emission spectrum and fluorescent quantum of above-mentioned material film at room temperature are determined respectively
Efficiency, and fluorescence emission spectrum and phosphorescence emission spectra (μ s of time delay 100) in 77K.Purple fluorescence material crystals,
Fluorescence emission wavelengths during room temperature in the film are 387nm, fluorescent emission ripple when absolute fluorescence quantum efficiency is 0.22,77K
Long and phosphorescence start wavelength is respectively 392 and 416nm, and corresponding singlet energy level and triplet are respectively 3.18 Hes
2.98eV, singlet-triplet difference is 0.20eV.
Claims (7)
1. a kind of purple fluorescence material crystals based on trifluoromethyl, it is characterised in that the material is 9- [3,5 two (fluoroforms
Base) phenyl] -9H- carbazoles, shown in structure such as formula (I)：
2. the purple fluorescence material crystals according to claim 1 based on trifluoromethyl, it is characterised in that mono-crystalline structures
In, crystallographic system is rhombic system, space group Pbca, crystallographic axis
Interplanar angle α=90.00 °, β=90.00 °, γ=90.00 °, elementary cell volume VElementary cellForUnit is brilliant
Molecular number (Z) in lattice is 8, and density (d) density is 1.533Mg/m3。
3. the purple fluorescence material crystals based on trifluoromethyl according to claim 1, it is characterised in that：In film during room temperature
In fluorescence emission wavelengths be 387nm, fluorescence quantum efficiency 0.22.
4. the purple fluorescence material crystals based on trifluoromethyl according to claim 1, it is characterised in that：Film is determined to exist
Fluorescence emission spectrum and phosphorescence emission spectra during 77K, time delay are 100 μ s；9- [3,5 two (trifluoromethyl) phenyl] -9H-
Carbazole fluorescence emission wavelengths in the film and phosphorescence start wavelength are respectively 392 and 416nm, corresponding singlet energy level and three
Line state energy level is respectively 3.18 and 2.98eV, and singlet-triplet difference is 0.20eV.
A kind of 5. preparation method of the purple fluorescence material crystals based on trifluoromethyl described in claim 1, it is characterised in that institute
Preparation method is stated to comprise the following steps：
With bromo- 3,5- bis- (trifluoromethyl) benzene of 1- for raw material, with carbazole, Anhydrous potassium carbonate, iodate Asia ketone, 1,10- phenanthroline one
Hydrate, DMF 1: 1~1.2: 1.5~2: 0.1~0.2: 0.1~0.2: 50~100 are carried out in molar ratio
It is well mixed, by mixture 20~40h of back flow reaction under nitrogen protection, reactant by plus water quenching go out, extract, column chromatography,
And the elution for the petroleum ether for boiling range being 60-90 DEG C, obtain 9- [3,5 two (trifluoromethyl) phenyl] -9H- carbazole solids；
By 9- [3,5 two (trifluoromethyl) phenyl] -9H- carbazole solids, with dichloromethane, ethanol in mass ratio 1: 40~80: 40
~80 carry out mixed dissolution, and room temperature solvent flashing obtains white needle-like crystals, and the white needle-like crystals are purple fluorescence material
Crystal.
6. the assay method of the purple fluorescence material crystals based on trifluoromethyl according to claim 5, it is characterised in that：Will
Material crystals described in claim 1 are dissolved in dichloromethane solution (1g/100mL) respectively, are then equably spin-coated on silicon chip
On, 50 DEG C of drying 30min, film is made.
7. the purple fluorescence material crystals based on trifluoromethyl described in a kind of claim 1, purple delayed fluorescence material can be used as
For electroluminescent device luminescent layer.
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| CN101688114A (en) * | 2007-07-05 | 2010-03-31 | 巴斯夫欧洲公司 | Organic light-emitting diodes comprising at least one disilyl compound selected from disilylcarbazoles, disilyldibenzofurans, disilyldibenzothiophenes, disilyldibenzophospholes, disilyldibenzothiophen |
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| CN103952139A (en) * | 2013-12-04 | 2014-07-30 | 宁波大学 | Tripyridine carbazole purple fluorescent material |
| US20150129849A1 (en) * | 2013-11-14 | 2015-05-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| JP2017128519A (en) * | 2016-01-19 | 2017-07-27 | 公益財団法人相模中央化学研究所 | Dialkyl[2-(pyrenyl)phenyl]phosphine, and catalyst comprising palladium compound and the same |
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2017
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| CN101688114A (en) * | 2007-07-05 | 2010-03-31 | 巴斯夫欧洲公司 | Organic light-emitting diodes comprising at least one disilyl compound selected from disilylcarbazoles, disilyldibenzofurans, disilyldibenzothiophenes, disilyldibenzophospholes, disilyldibenzothiophen |
| CN101878552A (en) * | 2007-07-05 | 2010-11-03 | 巴斯夫欧洲公司 | Organic light-emitting diodes containing carbene transition metal complex emitters and at least one compound selected from disilylcarbazoles, disilyldibenzofurans, disilyldibenzothiophenes, disilyldibenzophospholes, disilyldibenzothiophene s-oxides a |
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