CN1616429A - Red light emitting naphthyl imide compound and its synthetic method - Google Patents
Red light emitting naphthyl imide compound and its synthetic method Download PDFInfo
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Abstract
The present invention discloses a kind of red light emitting naphthyl imide compound. In the 4-place of 1, 8-naphthyl imide, aryl, especially aryl with electron donating performance, is introduced through unsaturated group to make the compound produce obvious fluorescence shift towards red light and emit bright red fluorescence. The compound may be used as the red light emitting material for organic electroluminescent device.
Description
Technical field
The present invention relates to a kind of naphthoyl imide compounds and synthetic method thereof, relate in particular to a kind of naphthoyl imide compounds that glows and synthetic method thereof.
Background technology
C.W.Tang in 1987 has prepared the organic electroluminescence device of high brightness, high-luminous-efficiency, low driving voltage, causes the very big interest of people to organic electroluminescence device again.Organic electroluminescent has low-voltage DC driving, active illuminating, vision is big, response speed is fast, rich color and low cost and other advantages, will progressively replace LCD (liquid-crystal display), PDP indicating meters such as (plasma displays), become the leading product of flat-panel monitor of future generation.Since the 1980s, external major company and research institution have just begun the research to electroluminescent organic material and device.Recent years, rapid to the research work progress of organic electroluminescent, there have been some small-sized organic electroluminescence devices to realize commercialization, be about to realize the scale operation of organic electroluminescence device soon.
Luminous organic material is an integral part crucial in the organic electroluminescence device, and luminous organic material has determined the application performances such as color, brightness, efficient and stability of organic electroluminescence device.In order to utilize organic electroluminescence to realize the demonstration of full color, ruddiness, green glow and the blue light electroluminescent material of must exploitation stable, high-level efficiency and high brightness.Up to the present, green-emitting and blue emitting material kind are more, have also found in actual applications to have the very green glow and the blue light material of high-luminous-efficiency and brightness.Compare with the ruddiness electroluminescent material with green glow, the luminescent material kind that glows is less, and luminous efficiency and luminosity are also lower.Oneself becomes the key of full color organic electroluminescence device practicability development the shortage of red illuminating material.The stability of luminescent material is a factor of reusing very much that influences electroluminescent device work-ing life and efficient, and the stability that therefore further improves luminous organic material also is one of key factor of organic electroluminescence device practicability.
1, the 8-naphthoyl imide compounds has excellent optical physics performance and higher fluorescence quantum efficiency, at aspects such as biological fluorescent labelling, white dyes, pH transmitter, laser, liquid crystal and electroluminescent important use is arranged.In general, the fluorescent emission wavelength of unsubstituted naphthalimide is shorter relatively, 1, introduce the maximum emission wavelength generation red shift that donor residuess such as alkoxyl group and substituted-amino can make fluorescence for 4 of the 8-naphthalimide, but the fluorescence of majority of compounds is mainly blueness and yellow, and naphthoyl imide compounds that can rubescent look fluorescence then seldom.
Summary of the invention
One of purpose of the present invention is, discloses a kind of novel naphthoyl imide compounds that glows;
Two of purpose of the present invention is, the synthetic method of above-claimed cpd is provided.
The said naphthoyl imide compounds that glows of the present invention, its general structure is as follows:
In the formula: R
1Be hydrogen, alkyl or aryl; N is 1～6; Ar is aromatic nucleus or aromatic amine; R
2Be hydrogen, alkyl, dialkyl amido, alkoxyl group or aryl.
Preferred compound is: R
1Be the alkyl of hydrogen, C1～C18 or the phenyl of replacement, preferred R
1Be hydrogen, methyl, ethyl, propyl group, butyl, amyl group, hexyl, heptyl, phenyl, tolyl, xylyl, butylbenzene base, tert-butyl-phenyl, di-tert-butyl-phenyl; N is 1～3; R
2Be alkyl, the alkoxyl group of C1～C8, the dialkyl amido of C1～C8, the phenyl or naphthyl of hydrogen, C1～C8, preferred R
2Be hydrogen, methyl, ethyl, propyl group, butyl, the tertiary butyl, methoxyl group, oxyethyl group, dimethylin, diethylin, dibutyl amino, phenyl or naphthyl; Ar is aromatic nucleus or the aromatic amine with following structure:
Above-claimed cpd synthetic can be adopted a kind of among method A or the method B:
Method A
Method B
The concrete reactions steps of method A or method B is, Compound I I (or IV) and compound III (or V) are mixed according to certain molar ratio, add the stirring solvent dissolving, by vacuumizing and the oxygen in the reaction mixture being removed towards the method for rare gas element, add catalyzer then, after 10 minutes to 72 hours, steaming desolventizes 0～150 ℃ of reaction, and residue is purified with the method for recrystallization or column chromatography.
Related R in the reaction equation
1, R
2, Ar and n be described identical with preamble, and X is chlorine, bromine or iodine, X is preferably bromine or iodine.
Used catalyzer is cuprous salt, palladium compound or aminated compounds in the reaction process.Wherein said cuprous salt is cuprous chloride, cuprous bromide or cuprous iodide, is preferably cuprous iodide; Said palladium compound is triphenylphosphine palladium chloride or tetraphenyl phosphine palladium; Aminated compounds is diethylamine, triethylamine, Diisopropylamine, tri-isopropyl amine, and tripropyl amine or Tributylamine are preferably triethylamine, Diisopropylamine or tri-isopropyl amine.
The mol ratio of Compound I I (or IV) and compound III (or V) is 1～10: 1 in the reaction process, is preferably 1～3: 1.
Used solvent is toluene, tetrahydrofuran (THF), dimethyl formamide or directly utilizes aminated compounds to be solvent in the reaction process.
Embodiment
The present invention is further elaborated below by embodiment, and the cited case does not limit protection scope of the present invention:
Embodiment 1
Synthesizing of 4-(3-methyl-3-hydroxyl-butynyl) triphenylamine:
In the 250ml there-necked flask, add 5.66g 4-iodine triphenylamine, 2ml 2-methyl-3-butyne-2-alcohol and 100ml triethylamine, stirring and dissolving, and with vacuumizing repeatedly and removing oxygen in the reaction vessel towards the method for argon gas, add the cuprous iodide of catalytic amount and triphenylphosphine palladium chloride then as catalyzer, reaction mixture was stirring at room 5 hours.After reaction finished, rotation was steamed and removed triethylamine, and residue is dissolved in the ethyl acetate, and washes with water three times, uses anhydrous magnesium sulfate drying, uses tetracol phenixin: ethyl acetate=10: 1 obtains the 3.73g product for eluent carries out column chromatography, and yield is 69%.
1H-NMR(CDCl
3)：δ1.60(s，6H)，2.37(s，1H)，6.94(m，2H)，7.00(t，2H)，7.07(d，4H)，7.25(m，6H)。
Embodiment 2
Synthesizing of 4-ethynyl triphenylamine:
In the 100ml there-necked flask, add 3.43g 4-(3-methyl-3-hydroxyl-butynyl) triphenylamine, 2.35g potassium hydroxide and 40ml Virahol, under argon shield, refluxed 4 hours.After reaction finished, the rotation solvent evaporated, residue was dissolved in the ethyl acetate, wash with water with after the hydrochloric acid soln washing 3 times again, the organic layer anhydrous magnesium sulfate drying, use methylene dichloride: sherwood oil=3: 1 carries out column chromatography, obtain the 2g product, yield is 71%.
1H-NMR(CDCl
3)：δ3.01(s，1H)，6.96(d，2H)，7.06(t，2H)，7.10(d，4H)，7.27(t，4H)，7.33(d，2H)。
Embodiment 3
Synthesizing of 4,4 '-two (3-methyl-3-hydroxyl-butynyl) triphenylamine:
In the 250ml there-necked flask, add 7g 4,4 '-diiodo-triphenylamine, 4.8ml 2-methyl-3-butyne-2-alcohol and 150ml triethylamine, stirring and dissolving, and with vacuumizing repeatedly and removing oxygen in the reaction vessel towards the method for argon gas, add the cuprous iodide of catalytic amount and triphenylphosphine palladium chloride then as catalyzer, reaction mixture reflux 7 hours.After reaction finished, rotation was steamed and removed triethylamine, and residue is dissolved in the ethyl acetate, and washes with water three times, uses anhydrous magnesium sulfate drying, uses tetracol phenixin: ethyl acetate=10: 1 obtains the 3.7g product for eluent carries out column chromatography, and yield is 65%.
1H-NMR(CDCl
3)：δ1.61(s，12H)，2.00(s，2H)，6.97(d，4H)，7.07(d，2H)，7.27(t，7H)。
Embodiment 4
4,4 '-diacetylene triphenylamine synthetic:
In the 100ml there-necked flask, add 1.8g4,4 '-two (3-methyl-3-hydroxyl-butynyl) triphenylamine, 1.5g potassium hydroxide and 50ml Virahol refluxed 4 hours under argon shield.After reaction finished, the rotation solvent evaporated, residue was dissolved in the ethyl acetate, wash with water with after the hydrochloric acid soln washing 3 times again, the organic layer anhydrous magnesium sulfate drying, use methylene dichloride: sherwood oil=3: 1 carries out column chromatography, obtain the 0.96g product, yield is 67%.
1H-NMR(CDCl
3)：δ3.02(s，2H)，7.00(d，4H)，7.09(d，2H)，7.31(t，7H)。
Embodiment 5
4,4 ', 4 "-three (3-methyl-3-hydroxyl-butynyl) triphenylamine is synthetic:
In the 100ml there-necked flask, add 3g 4,4 '; 4 "-triiodo triphenylamine, 1.6ml 2-methyl-3-butyne-2-alcohol and 70ml triethylamine, stirring and dissolving, and, add the cuprous iodide of catalytic amount and triphenylphosphine palladium chloride then as catalyzer, reaction mixture reflux 8 hours with vacuumizing repeatedly and removing oxygen in the reaction vessel towards the method for argon gas.After reaction finished, rotation was steamed and is removed triethylamine, and residue is dissolved in the ethyl acetate, and washes with water three times, uses anhydrous magnesium sulfate drying, and with dichloromethane alkanisation carbon: ethyl acetate=10: 1 obtains the 1.1g product for eluent carries out column chromatography, and yield is 60%.
1H-NMR(CDCl
3)：δ1.61(s，18H)，1.99(s，3H)，6.97(d，6H)，7.30(d，6H)。
Embodiment 6
4,4 ', 4 "-three the ethynyl triphenylamine is synthetic:
In the 100ml there-necked flask, add 1.1g 4,4 ', 4 "-three (3-methyl-3-hydroxyl-butynyl) triphenylamine, 1g potassium hydroxide and 60ml Virahol, refluxed 6 hours under argon shield.After reaction finished, the rotation solvent evaporated, residue was dissolved in the ethyl acetate, wash with water with after the hydrochloric acid soln washing 3 times again, the organic layer anhydrous magnesium sulfate drying, use methylene dichloride: sherwood oil=3: 1 carries out column chromatography, obtain the 0.45g product, yield is 64%.
1H-NMR(CDCl
3)：δ3.03(s，3H)，7.00(d，6H)，7.36(d，6H)。
Embodiment 7
N-butyl-4-ethynyl-1,8-naphthalimide synthetic:
With N-butyl-4-bromo-1, the 8-naphthalimide is a raw material, reacts according to the method for embodiment 1～6, obtains N-butyl-4-ethynyl-1, the 8-naphthalimide.
1H-NMR(CDCl
3)：
1H-NMR(CDCl
3)：δ0.98(t，3H)，1.46(m，2H)，1.73(m，2H)，3.69(s，1H)，4.19(t，2H)，7.85(t，1H)，7.96(d，1H)，8.57(d，1H)，8.66(d，1H)，8.74(d，1H)。
Embodiment 8
Naphthalimide I-1's is synthetic:
Method A:
In the 100ml there-necked flask; add 0.5g 4-ethynyl triphenylamine, 0.86g N-butyl-4-bromo-1; 8-naphthalimide and 70ml triethylamine; stirring and dissolving; add the cuprous iodide of catalytic amount and triphenylphosphine palladium chloride then as catalyzer; under argon shield, reaction mixture reflux 5 hours.After reaction finished, rotation was steamed and removed triethylamine, uses methylene dichloride: sherwood oil=2: 1 obtains 0.73g product I-1 for eluent carries out column chromatography, and yield is 76%.
Method B:
In the 100ml there-necked flask; add 0.74g 4-iodine triphenylamine, 0.55g N-butyl-4-ethynyl-1; 8-naphthalimide and 70ml triethylamine; stirring and dissolving; add the cuprous iodide of catalytic amount and triphenylphosphine palladium chloride then as catalyzer; under argon shield, reaction mixture reflux 5 hours.After reaction finished, rotation was steamed and removed triethylamine, uses methylene dichloride: sherwood oil=2: 1 obtains 0.8g product I-1 for eluent carries out column chromatography, and yield is 80%.
1H-NMR(CDCl
3)：δ0.98(t，3H)，1.46(m，2H)，1.73(m，2H)，4.19(t，2H)，7.06(d，2H)，7.13(t，2H)，7.16(d，4H)，7.31(t，4H)，7.50(d，2H)，7.82(t，1H)，7.91(d，1H)，8.54(d，1H)，8.64(d，1H)，8.72(d，1H)。
The maximum emission wavelength of this compound in methylene dichloride is λ
Max Fl=633nm is red fluorescence.
Embodiment 9
Naphthalimide I-2's is synthetic:
Method A:
In the 250ml there-necked flask; add 0.7g 4; 4 '-diacetylene triphenylamine, 1.9g N-butyl-4-bromo-1; 8-naphthalimide, 40ml triethylamine and 120ml tetrahydrofuran (THF); stirring and dissolving; add the cuprous iodide of catalytic amount and triphenylphosphine palladium chloride then as catalyzer, under argon shield, reaction mixture reflux 5 hours.After reaction finished, rotation was steamed and desolventized, and uses chloroform: sherwood oil=3: 1 obtains 0.9g product I-2 for eluent carries out column chromatography, and yield is 48%.
Method B:
In the 100ml there-necked flask; add 0.5g 4; 4 '-diiodo-triphenylamine, 0.55g N-butyl-4-ethynyl-1; 8-naphthalimide and 70ml triethylamine; stirring and dissolving; add the cuprous iodide of catalytic amount and triphenylphosphine palladium chloride then as catalyzer, under argon shield, reaction mixture reflux 7 hours.After reaction finished, rotation was steamed and removed triethylamine, uses chloroform: sherwood oil=3: 1 obtains 0.4g product I-2 for eluent carries out column chromatography, and yield is 52%.
1H-NMR(CDCl
3)：δ0.98(t，6H)，1.46(m，4H)，1.73(m，4H)，4.19(t，4H)，7.07(d，4H)，7.18(d，2H)，7.55(t，7H)，7.85(t，2H)，7.93(d，2H)，8.56(d，2H)，8.65(d，2H)，8.73(d，2H)。
The maximum emission wavelength of this compound in methylene dichloride is λ
Max Fl=621nm is red fluorescence.
Embodiment 10
Naphthalimide I-3's is synthetic:
Method A:
In the 100ml there-necked flask; add 0.35g 4; 4 '; 4 "-three ethynyl triphenylamines, 1.2g N-butyl-4-bromo-1; 8-naphthalimide, 15ml triethylamine and 45ml tetrahydrofuran (THF), stirring and dissolving adds the cuprous iodide of catalytic amount and triphenylphosphine palladium chloride then as catalyzer; under argon shield, reaction mixture reflux 8 hours.After reaction finished, rotation was steamed and is desolventized, and is that eluent carries out column chromatography with methylene dichloride, obtains 0.47g product I-3, and yield is 40%.
Method B:
In the 100ml there-necked flask; add 0.62g 4; 4 '; 4 "-triiodo triphenylamine, 0.83g N-butyl-4-ethynyl-1; 8-naphthalimide and 70ml triethylamine, stirring and dissolving adds the cuprous iodide of catalytic amount and triphenylphosphine palladium chloride then as catalyzer; under argon shield, reaction mixture reflux 7 hours.After reaction finished, rotation was steamed and is removed triethylamine, is that eluent carries out column chromatography with methylene dichloride, obtains 0.5g product I-3, and yield is 46%.
1H-NMR(CDCl
3)：δ0.98(t，9H)，1.46(m，6H)，1.73(m，6H)，4.19(t，6H)，7.21(d，6H)，7.64(d，6H)，7.85(t，3H)，7.96(d，3H)，8.57(d，3H)，8.66(d，3H)，8.74(d，3H)。
The maximum emission wavelength of this compound in methylene dichloride is λ
Max Fl=614nm is red fluorescence.
Embodiment 11
Naphthalimide I-4's is synthetic
Method A:
Method B:
Step according to embodiment 8 descriptions, with 4-methyl-4 '-ethynyl triphenylamine and N-butyl-4-bromo-1,8-naphthalimide employing method A reacts, or with 4-methyl-4 '-iodine triphenylamine and N-butyl-4-ethynyl-1,8-naphthalimide employing method B reacts, and obtains naphthalimide compound I-4.
1H-NMR(CDCl
3)：δ0.98(t，3H)，1.46(m，2H)，1.73(m，2H)，2.35(s，3H)，4.19(t，2H)，7.07(d，2H)，7.14(d，2H)，7.17(d，4H)，7.32(t，3H)，7.50(d，2H)，7.82(t，1H)，7.91(d，1H)，8.54(d，1H)，8.64(d，1H)，8.72(d，1H)。
The maximum emission wavelength of this compound in methylene dichloride is λ
Max Fl=635nm is red fluorescence.
Embodiment 12
Step according to embodiment 8 descriptions, with 4-methoxyl group-4 '-ethynyl triphenylamine and N-butyl-4-bromo-1,8-naphthalimide employing method A reacts, or with 4-methoxyl group-4 '-iodine triphenylamine and N-butyl-4-ethynyl-1,8-naphthalimide employing method B reacts, and obtains naphthalimide compound I-5.
1H-NMR(CDCl
3)：δ0.98(t，3H)，1.46(m，2H)，1.73(m，2H)，2.50(s，3H)，4.19(t，2H)，7.06(d，2H)，7.12(t，2H)，7.15(d，4H)，7.32(t，3H)，7.50(d，2H)，7.82(t，1H)，7.91(d，1H)，8.54(d，1H)，8.64(d，1H)，8.72(d，1H)。
The maximum emission wavelength of this compound in methylene dichloride is λ
Max Fl=636nm is red fluorescence.
Claims (7)
1, a kind of naphthoyl imide compounds that glows, its structure is shown in (I) formula:
In the formula: R
1Be hydrogen, alkyl or aryl; R
2Be hydrogen, alkyl, alkoxyl group, dialkyl amido or aryl; Ar is aromatic nucleus or aromatic amine; N is 1～6.
2, as the said compound of claim 1, it is characterized in that, wherein R
1Be the alkyl of hydrogen, C1～C18 or the phenyl of replacement; R2 is alkyl, the alkoxyl group of C1～C8, the dialkyl amido of C1～C8, the phenyl or naphthyl of hydrogen, C1～C8.
3, as the said compound of claim 2, it is characterized in that, wherein R
1Be hydrogen, methyl, ethyl, propyl group, butyl, amyl group, hexyl, heptyl, phenyl, tolyl, xylyl, butylbenzene base, tert-butyl-phenyl or di-tert-butyl-phenyl; R
2Be hydrogen, methyl, ethyl, propyl group, butyl, the tertiary butyl, methoxyl group, oxyethyl group, dimethylin, diethylin, dibutyl amino, phenyl or naphthyl; Ar is aromatic nucleus or the aromatic amine with following structure:
4, synthetic method as said any one compound in the claim 1～3 is characterized in that the key step of said synthetic method is as follows:
With Compound I I and compound III 1～10: 1 mixing in molar ratio, add the stirring solvent dissolving, after deoxygenation, add catalyzer, after 10 minutes to 72 hours, steaming desolventizes 0～150 ℃ of reaction, and residue is target compound through purification, and its reactional equation is as follows:
Wherein: X is chlorine, bromine or iodine; Said catalyzer is cuprous salt, palladium compound or aminated compounds.
5, as the said synthetic method of claim 4, it is characterized in that, wherein said catalyzer is cuprous chloride, cuprous bromide, cuprous iodide, triphenylphosphine palladium chloride, tetraphenyl phosphine palladium, diethylamine, triethylamine, Diisopropylamine, tri-isopropyl amine, tripropyl amine or Tributylamine.
6, synthetic method as said any one compound in the claim 1～3 is characterized in that the key step of said synthetic method is as follows:
With compound IV and compound V 1～10: 1 mixing in molar ratio, add the stirring solvent dissolving, after deoxygenation, add catalyzer, after 10 minutes to 72 hours, steaming desolventizes 0～150 ℃ of reaction, and residue is target compound through purification, and its reactional equation is as follows:
Wherein: X is chlorine, bromine or iodine; Said catalyzer is cuprous salt, palladium compound or aminated compounds.
7, as the said synthetic method of claim 6, it is characterized in that, wherein said catalyzer is cuprous chloride, cuprous bromide, cuprous iodide, triphenylphosphine palladium chloride, tetraphenyl phosphine palladium, diethylamine, triethylamine, Diisopropylamine, tri-isopropyl amine, tripropyl amine or Tributylamine.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102391496A (en) * | 2011-08-31 | 2012-03-28 | 上海大学 | Polyarylether light-emitting material with main chain containing naphthalimide and synthesis method thereof |
| CN103992305A (en) * | 2014-03-18 | 2014-08-20 | 四川大学 | Novel 1,8-naphthalimide derivative compound organic electroluminescent main material and device |
| US9383644B2 (en) | 2014-09-18 | 2016-07-05 | Heraeus Precious Metals North America Daychem LLC | Sulfonic acid derivative compounds as photoacid generators in resist applications |
| US9477150B2 (en) | 2015-03-13 | 2016-10-25 | Heraeus Precious Metals North America Daychem LLC | Sulfonic acid derivative compounds as photoacid generators in resist applications |
| CN107652280A (en) * | 2017-11-02 | 2018-02-02 | 台州学院 | One kind has 1,8 naphthalimide compounds and its synthetic method of red fluorescence |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7259260B2 (en) * | 2001-10-22 | 2007-08-21 | Mitsui Chemicals, Inc. | Imide compound and optical recording media made by using the same |
| JP2004082439A (en) * | 2002-08-26 | 2004-03-18 | Mitsui Chemicals Inc | Optical recording medium and diaryl acetylenic compound |
-
2004
- 2004-09-15 CN CNB2004100664155A patent/CN1295219C/en not_active Expired - Fee Related
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102391496A (en) * | 2011-08-31 | 2012-03-28 | 上海大学 | Polyarylether light-emitting material with main chain containing naphthalimide and synthesis method thereof |
| CN103992305A (en) * | 2014-03-18 | 2014-08-20 | 四川大学 | Novel 1,8-naphthalimide derivative compound organic electroluminescent main material and device |
| CN103992305B (en) * | 2014-03-18 | 2017-05-17 | 四川大学 | 1,8-naphthalimide derivative compound organic electroluminescent main material and device |
| US9383644B2 (en) | 2014-09-18 | 2016-07-05 | Heraeus Precious Metals North America Daychem LLC | Sulfonic acid derivative compounds as photoacid generators in resist applications |
| US9477150B2 (en) | 2015-03-13 | 2016-10-25 | Heraeus Precious Metals North America Daychem LLC | Sulfonic acid derivative compounds as photoacid generators in resist applications |
| US9709886B2 (en) | 2015-03-13 | 2017-07-18 | Heraeus Precious Metals North America Daychem LLC | Sulfonic acid derivative compounds as photoacid generators in resist applications |
| CN107652280A (en) * | 2017-11-02 | 2018-02-02 | 台州学院 | One kind has 1,8 naphthalimide compounds and its synthetic method of red fluorescence |
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| Publication number | Publication date |
|---|---|
| CN1295219C (en) | 2007-01-17 |
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