CN101781234B - Triphenylethylene compound containing cyanogen and preparation method thereof - Google Patents
Triphenylethylene compound containing cyanogen and preparation method thereof Download PDFInfo
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- CN101781234B CN101781234B CN 201010143337 CN201010143337A CN101781234B CN 101781234 B CN101781234 B CN 101781234B CN 201010143337 CN201010143337 CN 201010143337 CN 201010143337 A CN201010143337 A CN 201010143337A CN 101781234 B CN101781234 B CN 101781234B
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Abstract
The invention provides a triphenylethylene compound containing cyanogen. An electron repulsive group comprising bis-phenylamino and alkoxy and an electron withdrawing group comprising the cyanogen are led to a triphenyl ethane conjugated system to form to two electron transfer channels opposite to each other. The triphenylethylene compound provided by the invention has obvious intramolecular charge transfer property. Due to the influence of the three phenyl, four bis-phenylamino and two alkoxyl steric clashes in the triphenylethylene compound, the molecular space structure of the triphenylethylene compound containing the cyanogen provided by the invention is of a curved petal shape of orchid, and having gathered auxoflorence property.
Description
Technical field
The invention belongs to the organic photoelectric functional material field.The present invention be more particularly directed to a kind of triphenylethylene compound containing cyanogen and preparation method thereof.
Technical background
The scientific and technological circle of some developed countries and industrial community have been paid much attention to the organic photoelectric luminescent device (OLED/PLED) made by conjugation organic molecule or polymer macromolecule, because OLED/PLED has low cost of manufacture, the various features such as color and luster is abundant, brightness is high, flexible demonstration.Yet, it is in highly concentrated solution or when solid-state that existing luminous organic material faces a bottleneck problem, the luminous organic material molecule presents the close-packed of H-clustered pattern (face-face), intermolecular strong interaction is easy to cause strong non-radiative decay, causes its luminous efficiency solid-state or state of aggregation to be compared with its lower concentration dilute solution and is order of magnitude decline.Calendar year 2001, Tang Benzhong (Chem.Commmun., 2001,1740) chance on Silole (siloles) in dilute solution photoluminescence extremely a little less than, but luminous intensity increases phenomenon (aggregation-induced emissionenhancement, AIEE) when solid state powder or film.The luminous strongthener of this gathering has thoroughly solved the fluorescent quenching phenomenon that the organic photoelectric luminescent material easily causes when solid-state, so assemble the important directions that luminous strongthener becomes the research of organic photoelectric luminescent material.So far people find that successively the conjugation organic molecule of some J-clustered patterns (head-tail) has the luminous enhancing characteristic of gathering, comprise substituted diphenylamine ethene { Chem.Eur.J., 2004. (10): 791}, tetraphenyl ethylene compounds { J.Mater.Chem., 2004, (10): 1471}, diphenylethyllene benzene { J.Phys.Chem.B, 2006, (110): 20993}.CN10133539 and CN101343534 also disclose the triphenyl vinyl compound and the dendritic compound of anthracene-triphenylamine has the characteristic of the luminous enhancing of molecular aggregates.These a small amount of achievements in research show when state of aggregation, and it is its key factor with the luminous enhancing characteristic of molecular aggregates that by force, there is not intermolecular H-clustered pattern (molecule steric barrier, dendritic or spirrillum molecular configuration) in the molecular structure rigidity of conjugation organic molecule.
At present people also have realized that in the conjugated system of organic molecule or polymer macromolecule and introduce carrier transport group (cavity transmission group triphenylamine base, carbazyl, thiophene etc. and electric transmission group benzoxazole, oxadiazole, Ben Bing oxadiazole, triazine ring etc.) or push-and-pull electron group, can strengthen its intramolecular charge transport ability, improve organic conjugate small molecules or conjugated polymers macromole fluorescence quantum yield (Acta Chim.Sin., 2005,63 (6): 460; Synthetic Metals, 2003,132 (2): 145; Photographic Science﹠amp; PhotoChemistry, 2001,19 (1): 9).
Based on above experiment and theoretical research result, the factors such as effect of winning over by any means of the molecular structure of analysis-by-synthesis conjugation organic molecule, conformation, molecular dipole, intermolecular accumulation mode or environment molecule are on the impact of its luminous intensity and quantum yield, the invention provides a kind of triphenylethylene compound containing cyanogen, purpose is to find a kind of chemical structure novelty, intramolecular charge to shift strongly, have the luminous enhancing characteristic of gathering, the synthetic easy conjugation organic molecule luminescent material of production method, further promotes OLED industrialized developing process and commercial applications process.
Summary of the invention
The invention provides a kind of cyano group ALIPHATIC CYCLIC MOIETY AND that contains, have structure shown in the general formula (I):
General formula (I)
R in its formula of (I)
1And R
2Be selected from respectively C
1～C
20Alkyl.
A kind of triphenylethylene compound containing cyanogen molecule provided by the invention has following characteristics:
1. electron donating group (diphenylamino and alkoxyl group) and drawing electron group (cyano group) have been accessed in the triphenyl vinyl conjugated system, four diphenylamino of triphenyl vinyl conjugated system head end and two alkoxyl groups are respectively to triphenyl vinyl conjugated system supplied for electronic, be positioned at two cyano group on the triphenyl vinyl conjugated system to drawing electronics, form the transfer transport passage of two relative directions, shifted character so a kind of triphenylethylene compound containing cyanogen provided by the invention has obvious intramolecular charge.
2. by the minimum internal energy of molecular simulation of Chem3D Ultra8.0, three phenyl at prompting vinyl two ends are large owing to being subject to spatial volume, fully two dimensional structure.Because four diphenylamino of triphenyl vinyl conjugated system head end also are subject to sterically hindered impact, show that the triphenylethylene compound containing cyanogen spatial configuration of molecules presents the butterfly orchid petal-shaped and has the hand-type feature.
A kind of triphenylethylene compound containing cyanogen raw materials of structure shown in the general formula provided by the invention (I) is selected from pentanoic, 4,4 '-difluoro benzophenone, 2,5-diakoxy-1,4-benzene diacetonitrile.According to raw materials of the present invention, the preparation method of a kind of triphenylethylene compound containing cyanogen of structure comprises two synthesis steps shown in the general formula of the present invention (I):
Step 14,4 '-two (diphenylamino) benzophenone intermediate synthetic
Of the present invention 4, the synthetic of 4 '-two (diphenylamino) benzophenone intermediate is to adopt pentanoic and 4, the nucleophilic substitution reaction of 4 '-difluoro benzophenone (seeing that reaction formula 1.), synthesis condition is easy to control, the reaction product yield is high and be easy to purify, while pentanoic of the present invention and 4,4 '-difluoro benzophenone all has supply of commodities, wide material sources.
Reaction conditions and the schedule of operation optimized are: in organic solvent, drop in advance alkali reagent and pentanoic, heat up 60～80 ℃, stirred 0.5～4 hour.This purpose is that pentanoic is converted into the diphenylamino negative ion.After this, add again 4,4 '-difluoro benzophenone, 100～160 ℃ of temperature controls, stirring reaction 6～12 hours.The conventional separation and purification means such as after reaction finished, employing was concentrated, filtration, recrystallization, drying can make 4,4 '-two (diphenylamino) benzophenone intermediate.
Organic solvent of the present invention refers to a kind of in pentanoic, glycol dimethyl ether, ethylene glycol diethyl ether, methyl-sulphoxide, DMF, N,N-dimethylacetamide, the hexamethylphosphoramide, preferred hexamethylphosphoramide.Consumption of organic solvent of the present invention is 4,3～30 times of 4 '-difluoro benzophenone quality.
Alkali reagent of the present invention refers to a kind of in diisopropylamino lithium, n-Butyl Lithium, lithium borohydride, lithium aluminium hydride, sodium phenide, sodium hydride, sodium borohydride, hydrolith, phenyl-magnesium-bromide, sodium tert-butoxide or the potassium tert.-butoxide.Optimize sodium tert-butoxide.
Alkali reagent of the present invention, pentanoic and 4, the mole dosage optimal control of 4 '-difluoro benzophenone is 2.0～2.5: 2.0～2.5: between 1.
Synthesizing of step 2 triphenylethylene compound containing cyanogen
Of the present invention 2,5-dialkoxy-1, contain two active methylene groups in the 4-benzene diacetonitrile molecule, in organic solvent, be subjected to the katalysis of alkali reagent, 4,4 '-two (diphenylamino) benzophenone intermediate generation condensation reaction that can make with step 1, structure shown in preparation general formula (I) contain cyanogen triphenyl vinyl compound, concrete reaction sees that reaction formula is 2..
Reaction conditions and the schedule of operation optimized are: in organic solvent, drop into 2,5-diakoxy-1,4-benzene diacetonitrile and 4,4 '-two (diphenylamino) benzophenone intermediate and alkali reagent, 60～130 ℃ of stirrings of temperature control 6～12 hours.After reaction finishes, adopt the separation and purification means of the routines such as concentrated, filtration, washing, recrystallization, drying, can make the triphenylethylene compound containing cyanogen of structure shown in the general formula (I).
Organic solvent of the present invention refers to a kind of in glycol dimethyl ether, ethylene glycol diethyl ether, methyl-sulphoxide, DMF, N,N-dimethylacetamide, the hexamethylphosphoramide, preferred hexamethylphosphoramide.Consumption of organic solvent of the present invention is 4,3～30 times of 4 '-two (diphenylamino) benzophenone intermediate quality.
Alkali reagent of the present invention refers to a kind of in diisopropylamino lithium, n-Butyl Lithium, lithium borohydride, sodium phenide, sodium hydride, sodium borohydride, hydrolith, phenyl-magnesium-bromide, sodium tert-butoxide or the potassium tert.-butoxide.Optimize sodium tert-butoxide.
Alkali reagent of the present invention, 2,5-diakoxy-1,4-benzene diacetonitrile and 4, the mole dosage of 4 '-two (diphenylamino) benzophenone intermediate is controlled at 2.0～3.5: 2.0～2.5: 1.
Specific embodiment
By following embodiment a kind of triphenylethylene compound containing cyanogen of general formula provided by the invention (I) and preparation method thereof is further specified, its purpose is to understand better content of the present invention.Therefore, unlisted other general formula (I) triphenylethylene compound containing cyanogen and preparation method thereof should not be considered as limiting the scope of the invention among the embodiment.
The preparation of embodiment 1 triphenylethylene compound containing cyanogen I-1
Step 14, synthesizing of 4 '-two (diphenylamino) benzophenone intermediate: in the four-hole reaction flask of agitator is housed, add 30 milliliters of hexamethylphosphoramides, 8.5 gram (0.05 mole) pentanoic and 0.052 mole of sodium tert-butoxide, dispersed with stirring is even, N
2Lower 60～80 ℃ of insulations that heat up of protection eliminated the trimethyl carbinol in 2 hours.After this add in batches 4.4 gram (0.02 moles) 4,4 '-difluoro benzophenone, 100～130 ℃ of reactions finished in 6 hours.The reaction product system is cooled to room temperature, add ethanol, leave standstill crystallization, filter, use ethanol/acetone (volume ratio V/V=3/7) mixed solvent to the filter cake recrystallization, vacuum-drying makes yellow 4,4 '-two (diphenylamino) benzophenone intermediate of 11.75 grams, productive rate 91.7%, 173～175 ℃ of fusing points.Ultimate analysis: C
37H
28N
2O measured value (calculated value): C85.99 (86.02), H5.44 (5.46), N5.37 (5.42).
Step 2 triphenylethylene compound containing cyanogen I-1's is synthetic: in the four-hole reaction flask of agitator is housed, add 10.6 grams 4,4 '-two (diphenylamino) benzophenone intermediate and 2.2 grams 2,5-dimethoxy-1,4-benzene diacetonitrile, with the dissolving of 70 milliliters of ethylene glycol diethyl ethers, stir the lower ethylene glycol diethyl ether solution that contains 0.025 mole of sodium tert-butoxide that adds in batches, 75 ℃ of stirring reactions 12 hours.In the reaction system impouring ethanol, leave standstill crystallization, filter, filter cake uses the dimethylbenzene recrystallization, makes the triphenylethylene compound containing cyanogen I-1 of 11.03 gram bright greens, productive rate 91.9%.The TGA method records Tg161 ℃, and the DSC method records Td455 ℃.Ultimate analysis: C
86H
64N
6O
2Measured value (calculated value): C85.11 (85.12), H5.29 (5.32), N6.88 (6.93).H
1-NMR(DMSO-d
6)δ：1.32(s，6H)，6.52～7.24(m，58H)。EI-MS(m/e)：1212.5(M，100％)。Concentration is 4.5 * 10
-5The triphenylethylene compound containing cyanogen I-1 xylene solution Ultraviolet-visible Spectroscopic Characteristics peak λ max=402nm of mol/L, excitation wavelength is the fluorescence spectral characteristic peak λ max=495nm of 400nm.
The preparation of embodiment 2 triphenylethylene compound containing cyanogen I-2
Preparation method and schedule of operation according to embodiment 1, with the raw material 2 of step 2 among the embodiment 1,5-dimethoxy-Isosorbide-5-Nitrae-benzene diacetonitrile changes 2-methoxyl group-5-n-butoxy-1,4-benzene diacetonitrile just can make bright green triphenylethylene compound containing cyanogen I-2 of the present invention.The TGA method records Tg121 ℃, and the DSC method records Td450 ℃.Its concentration is 4.5 * 10
-5The xylene solution Ultraviolet-visible Spectroscopic Characteristics peak λ max=402nm of mol/L, excitation wavelength is the fluorescence spectral characteristic peak λ max=494nm of 400nm.
The preparation of embodiment 3 triphenylethylene compound containing cyanogen I-3
According to preparation method and the schedule of operation of embodiment 1, with the raw material 2 of embodiment 1 step 2,5-dimethoxy-1,4-benzene diacetonitrile changes 2,5-two neopentyl oxygens-Isosorbide-5-Nitrae-benzene diacetonitrile just can make bright green triphenylethylene compound containing cyanogen I-3 of the present invention.The TGA method records Tg102 ℃, and the DSC method records Td435 ℃.Its concentration is 4.5 * 10
-5The xylene solution Ultraviolet-visible Spectroscopic Characteristics peak λ max=401nm of mol/L, excitation wavelength is the fluorescence spectral characteristic peak λ max=496nm of 400nm.
The fluorescent characteristics of embodiment 4 triphenylethylene compound containing cyanogen I-1～3
Use dimethylbenzene/methanol mixed solvent respectively configuration concentration is 4.5 * 10
-5Mol/L triphenylethylene compound containing cyanogen I-1～3 solution, the consumption mass ratio of mixed solvent dimethylbenzene/methyl alcohol is 100: 0,75: 25 and 50: 50, observe respectively fluorescence spectrum spectral signature peak (λ max) and the fluorescence intensity (I) of triphenylethylene compound containing cyanogen I-1 of the present invention～3 solution, the result shows that triphenylethylene compound containing cyanogen I-1～3 have all that to assemble fluorescence enhanced propertied, can be used as the organic molecule luminescent material, see Table 1.
The fluorescence spectral characteristic of table 1 I-1～3
Claims (2)
1. triphenylethylene compound containing cyanogen, the structure shown in (I) that it is characterized in that having general formula:
General formula (I)
R in its formula of (I)
1And R
2Be selected from respectively C
1～C
20Alkyl.
2. according to the preparation method of a kind of triphenylethylene compound containing cyanogen claimed in claim 1, it is characterized in that comprising two synthesis steps:
Step 14,4 '-two (diphenylamino) benzophenone intermediate synthetic
The chemosynthesis principle of 4,4 '-two (diphenylamino) benzophenone intermediate sees that reaction formula is 1.:
Schedule of operation is: in organic solvent, drop in advance alkali reagent and pentanoic, heat up 60～80 ℃, stirred 0.5～4 hour, after this, add again 4,4 '-difluoro benzophenone, 100～160 ℃ of temperature controls, stirring reaction 6～12 hours after reaction finishes, adopts concentrated, filtration, recrystallization, dry separation and purification means, make 4,4 '-two (diphenylamino) benzophenone intermediate;
Wherein:
Described organic solvent refers to a kind of in pentanoic, glycol dimethyl ether, ethylene glycol diethyl ether, methyl-sulphoxide, DMF, N,N-dimethylacetamide or the hexamethylphosphoramide;
Described consumption of organic solvent is 4,3～30 times of 4 '-difluoro benzophenone quality;
Described alkali reagent refers to a kind of in diisopropylamino lithium, n-Butyl Lithium, lithium borohydride, lithium aluminium hydride, sodium phenide, sodium hydride, sodium borohydride, hydrolith, phenyl-magnesium-bromide, sodium tert-butoxide or the potassium tert.-butoxide;
Described alkali reagent, pentanoic and 4, the mole dosage of 4 '-difluoro benzophenone are 2.0～2.5: 2.0～2.5: 1;
Synthesizing of step 2 triphenylethylene compound containing cyanogen
The cyanogen triphenyl vinyl compound chemosynthesis principle that contains of structure shown in the general formula (I) sees that reaction formula is 2.:
②
Schedule of operation is: in organic solvent, drop into 2,5-dialkoxy-1,4-benzene diacetonitrile and 4,4 '-two (diphenylamino) benzophenone intermediate and alkali reagent, 60～130 ℃ of temperature controls, stirred 6～12 hours, after reaction finishes, adopt concentrated, filtration, washing, recrystallization, drying, make the triphenylethylene compound containing cyanogen of structure shown in the general formula (I);
Wherein:
The R of described reaction formula in 2.
1And R
2Be selected from respectively C
1～C
20Alkyl;
Described organic solvent refers to a kind of in glycol dimethyl ether, ethylene glycol diethyl ether, methyl-sulphoxide, DMF, N,N-dimethylacetamide or the hexamethylphosphoramide;
Described consumption of organic solvent is 4,3～30 times of 4 '-two (diphenylamino) benzophenone intermediate quality;
Described alkali reagent refers to a kind of in diisopropylamino lithium, n-Butyl Lithium, lithium borohydride, sodium phenide, sodium hydride, sodium borohydride, hydrolith, phenyl-magnesium-bromide, sodium tert-butoxide or the potassium tert.-butoxide;
Described alkali reagent, 2,5-diakoxy-1,4-benzene diacetonitrile and 4, the mole dosage of 4 '-two (diphenylamino) benzophenone intermediate is 2.0～3.5: 2.0～2.5: 1.
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| CN113429336B (en) * | 2021-07-22 | 2022-12-13 | 京东方科技集团股份有限公司 | Organic electroluminescent material, light-emitting device and application |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1090911A2 (en) * | 1999-10-06 | 2001-04-11 | Sony Corporation | Bis(aminostyryl) anthracene compound, synthesis intermediate thereof, and process for production thereof |
| CN101343537A (en) * | 2008-08-14 | 2009-01-14 | 中山大学 | Synthesis of novel organic luminescent material containing triphenylethylene carbazole derivant structure and application thereof |
| CN101659865A (en) * | 2009-09-16 | 2010-03-03 | 中山大学 | Gathering induced luminescence material containing triphenyl thylene structure, synthesis method and application thereof |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1090911A2 (en) * | 1999-10-06 | 2001-04-11 | Sony Corporation | Bis(aminostyryl) anthracene compound, synthesis intermediate thereof, and process for production thereof |
| CN101343537A (en) * | 2008-08-14 | 2009-01-14 | 中山大学 | Synthesis of novel organic luminescent material containing triphenylethylene carbazole derivant structure and application thereof |
| CN101659865A (en) * | 2009-09-16 | 2010-03-03 | 中山大学 | Gathering induced luminescence material containing triphenyl thylene structure, synthesis method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| Plater, M. John等.Polyaromatic amines. Part 3: Synthesis of poly(diarylamino)styrenes and related compounds.《Tetrahedron》.2003,第59卷(第25期),4673-4685. * |
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