CN1301971C - Red organic electrofluorescence material based on N-aryl carbazole and its preparation method - Google Patents
Red organic electrofluorescence material based on N-aryl carbazole and its preparation method Download PDFInfo
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Abstract
The present invention relates to a red luminescent material for organic electroluminescence and a preparation method thereof, which belongs to the technical field of organic electroluminescent materials. The material has a basic structure of N-aromatic carbazole; multiple identical chromophores-conjugated multi-nitrile is contained in molecules. The extensibility of the N-aromatic carbazole in a three-dimensional space can decrease the agglomeration effect among the molecules and reduce the self-quenching phenomenon of the red luminescent material. The molecules have preferable cavity transmission characteristics and high glass transition temperature, and are capable of forming amorphous films with high stability and favorable uniformity. Consequently, the luminescent material can be used for manufacturing red organic electroluminescent devices or manufacturing full color organic electroluminescent devices together with other materials. The material also has wide application prospects in other photoelectric devices.
Description
Technical field
The invention belongs to the electroluminescent organic material technical field, be specially a kind of red illuminating material that is used for organic electroluminescent and preparation method thereof.
Technical background
Organic electroluminescent has characteristics such as low dc voltage driving, brightness height, visual angle be wide, is considered to one of most promising plane of future generation technique of display (C.W.Tang and S.A.VanSlyke.Appl.Phys.Lett., 1987,51 (12): 913-915).The organic molecule electroluminescent device needs two-layer with the upper film composition mostly, and they have electronics and cavity transmission ability respectively.The performance of organic molecule depends on its structure, its carrier transmission characteristics is relevant with the conjugated system of molecule, the polyaromatic conjugated system often has electronic transmission performance, and N-aryl carbazole quasi-molecule has extensibility on three-dimensional space, sterically hindered big, have cavity transmission ability, can pass through molecular designing, obtain luminescent organic molecule material of a great variety, that performance is different.The red organic electrofluorescence material that uses is the derivative of DCM mostly at present, this type of molecular polarity is bigger, clustering effect of molecules can produce concentration quenching under high doping, thereby this type of material can only be as the object luminescent material, be entrained in and make luminescent device in the electron transport material, and the slight change meeting of doping content causes emission wavelength to move, and this has brought difficulty for the luminescent device of making stable performance.In polar molecule, introduce sterically hindered big group, can reduce by intermolecular bunch of collection effect, reduce the self quenching phenomenon of red illuminating material, improve the luminescent properties of red illuminating material.Present widely used red illuminating material DCJTB is exactly the DCM derivative (C.H.Chen by this thinking design, C.W.Tang, J.Shi andK.P.Klubek.Macromol.Symp., 1997,125:49-58), but its preparation method is loaded down with trivial details, and raw material is rare, the cost height, scale operation and application are had any problem.
Summary of the invention
The object of the present invention is to provide a kind of easy to prepare, reasonable price, stable performance based on red organic electrofluorescence material of N-aryl carbazole and preparation method thereof.
The object of the present invention is to provide the Application Areas of above-mentioned materials.
Red organic electrofluorescence material provided by the invention is the derivative of hole mobile material N-aryl carbazole, contains a plurality of identical chromophoric groups---conjugation nitrile, and its structure is as follows:
Wherein, Ar is a phenyl or naphthyl, and the n value is 0 or 1.
Work as n=1, when Ar was naphthyl, the compound molecule formula was C
34H
27N
3, being designated as NNCa-2CN, structural formula is:
Chinese: 3-2-(3,3-dinitrile methylene radical-5,5-dimethyl-1-cyclohexenyl) vinyl-N-naphthyl-carbazole;
English name: 3-2-(3,3-dicyanomethylene-5,5-dimethyl-1-cyclohexylidene) vinyl-N-naphthyl-carbazole.
Work as n=1, when Ar was phenyl, the compound molecule formula was C
31H
25N
3, being designated as PNCa-2CN, structural formula is:
Chinese: 3-2-(3,3-dinitrile methylene radical-5,5-dimethyl-1-cyclohexenyl) vinyl-N-phenyl-carbazole;
English name: 3-2-(3,3-dicyanomethylene-5,5-dimethyl-1-cyclohexylidene) vinyl-N-phenyl-carbazole.
Work as n=0, when Ar was phenyl, the compound molecule formula was C
44H
37N
5, being designated as PNCa-4CN, structural formula is:
Chinese: 3,6-two (2-(3,3-dinitrile methylene radical-5,5-dimethyl-1-cyclohexenyl) vinyl)-N-phenyl-carbazole;
English name: 3,6-bis (2-(3,3-dicyanomethylene-5,5-dimethyl-1-cyclohexylidene) vinyl-N-phenyl-carbazole.
Work as n=0, when Ar was naphthyl, the compound molecule formula was C
48H
41N
5, being designated as NNCa-4CN, structural formula is:
Chinese: 3,6-two (2-(3,3-dinitrile methylene radical-5,5-dimethyl-1-cyclohexenyl) vinyl)-N-naphthyl-carbazole;
English name:
3，6-bis(2-(3，3-dicyanomethylene-5，5-dimethyl-1-cyclohexylidene)vinyl-N-naphthyl-carbazole.
The invention allows for the synthetic method of this molecule, utilization Knoevenagel condensation reaction is in system of the present invention.Reaction generates intermediate product (being designated as M) by isophorone (being designated as I) and propane dinitrile (being designated as II), and without separation, direct and N-aryl carbazole aldehyde derivatives (III) reaction obtains target molecule, and concrete steps are as follows:
To wait a mole isophorone (I) and propane dinitrile (II) to be dissolved in a certain amount of glacial acetic acid, aceticanhydride, piperidines and the DMF solvent, the mol ratio of mixed solvent is 2.5: 1 successively: (4-4.5): (450-500), react after 0.5-2 hour, add triarylamine aldehyde derivatives (III), continue reaction 0.5-2 hour, pour into while hot in the water, the solid of separating out is through recrystallization or column chromatography purification, get the purple solid, productive rate 52%-66%.The reactant molar ratio example is: I: II: III=1: 1: 0.1-1, and temperature of reaction is 25-100 ℃, one step of reaction finishes.
Product postprocessing, separation and purification are art methods, and those skilled in the art all can realize.
The present invention gives the preparation method of reactant III, the N-aryl carbazole in the presence of Phosphorus Oxychloride by dimethyl formamide formylation (Vilsmeier reaction).
Material of the present invention can be used to make red organic electroluminescence device.
Material of the present invention is made into organic electroluminescence device, and the preparation method is identical with the prior art bibliographical information.
The red illuminating material that the present invention obtains has following characteristics: one, molecule derivatize on hole mobile material N-aryl carbazole basis produces, and has carrier transmission characteristics preferably; Two, the extensibility of N-aryl carbazole structure on three-dimensional space can be eliminated clustering effect of molecules, reduces the self quenching phenomenon of red illuminating material; Three, with containing a plurality of identical chromophoric groups in a part, can improve the luminous efficiency of molecule; Four, second-order transition temperature height can form the unformed film of thermostability height, good uniformity.Therefore, can make redness or make full-color organic electroluminescent devices with these luminescent materials with other material-mix.Easy, the reasonable price of the inventive method, this material also has wide practical use in other opto-electronic device.
Description of drawings
Fig. 1 is the luminescent spectrum distribution plan of embodiment 2 (NNCa-2CN).
Fig. 2 is the chromaticity coordinates figure of Fig. 1.
Embodiment
The invention is further illustrated by the following examples.
Embodiment 1, the preparation of 3-carboxaldehyde radicals-N-naphthyl-carbazole: add 2.93g (10.0mmol) N-naphthyl carbazole, 1.9ml (24.5mmol) DMF and 20ml 1 in the 100ml eggplant-shape bottle, the 2-ethylene dichloride.Reaction flask places ice-water bath, stirs to drip 2.3ml (24.5mmol) POCl down
3Finish, in 95 ℃ of oil baths, refluxed 21 hours, pour into while hot in the 150ml frozen water, with 1M NaOH solution regulator solution pH to 7.Ethyl acetate extraction, drying is removed on the Rotary Evaporators and is desolvated.Column chromatography purification (leacheate: toluene), obtain light yellow product 1.02g (productive rate 31.9%).
IR(KBr，cm
-1)：2820，2720，1686，875，840，805，769，700。
1H-NMR(CDCl
3，500MHz)：δ10.13(s，1H)，8.74(s，1H)，8.27(q，J＝3.8Hz，1H)，8.09(d，J＝8.1Hz，1H)，8.04(d，J＝8.2Hz，1H)，7.88(q，J＝7.4Hz，1H)，7.69(t，J＝7.7Hz，1H)，7.65(d，J＝6.6Hz，1H)，7.56(t，J＝7.7Hz，1H)，7.40-7.38(m，2H)，7.34(t，J＝7.6Hz，1H)，7.19(d，J＝8.6Hz，1H)，7.05(q，J＝7.4Hz，2H)。
Embodiment 2, the preparation of NNCa-2CN: add 1.9ml (12.7mmol) isophorone and 0.80g (12.1mmol) propane dinitrile in 50ml eggplant type bottle.0.08ml glacial acetic acid and 0.06ml aceticanhydride are dissolved in 10ml DMF, get 1.8ml and add reaction flask, the 0.44ml piperidines is dissolved in 5ml DMF, get 1.8ml and add reaction flask, stirring at room 1 hour, being warming up to 80 ℃ again stirred 1 hour, add 1.00g (3.1mmol) 3-carboxaldehyde radicals-N-phenyl-carbazole, continue to stir 1.5 hours, pour into while hot in the 150ml hot water of (containing the dense HCl of 5ml), collect and separate out solid, crude product stirs in 50ml Virahol and 7ml water, suction filtration is collected solid, and re-crystallizing in ethyl acetate gets red product 0.70g (productive rate 52.7%).
IR(KBr，cm
-1)：2958，2213，1390，893，801，763，750，700。
1H-NMR(CDCl
3，500MHz)：8.36(s，1H)，8.23(t，J＝7.2Hz，1H)，8.08(d，J＝8.2Hz，1H)，8.04(d，J＝8.3Hz，1H)，7.69(t，J＝7.9Hz，1H)，7.64(d，J＝7.3Hz，1H)，7.55(q，J＝9.9Hz，2H)，7.38-7.33(m，3H)，7.28(d，J＝16.0Hz，1H)，7.25(d，J＝12.5Hz，1H)，7.08(d，J＝16.0Hz，1H)，7.01(t，J＝7.5Hz，2H)，6.87(s，1H)，2.62(s，2H)，2.54(s，1H)，1.11(s，1H)。
Solid photoluminescence (film, excitation wavelength 405nm): peak wavelength 630nm, peak width at half height 126nm;
Chromaticity coordinates: x=0.639, y=0.359.
MS(EI)：m/e?491(M
+)。
Ultimate analysis: calculated value (C
35H
27N
3) C, 85.85; H, 5.57; N, 8.58.Measured value: C, 85.94; H, 5.39; , N, 8.46.
Embodiment 3, the preparation of 3-carboxaldehyde radicals-N-phenyl-carbazole: add 1.48g (5.1mmol) N-phenyl carbazole, 1.2ml (15.5mmol) DMF and 20ml 1 in the 100ml eggplant-shape bottle, the 2-ethylene dichloride.Reaction flask places ice-water bath, stirs to drip 1.5ml (15.5mmol) POCl down
3Finish, in 95 ℃ of oil baths, refluxed 21 hours, pour into while hot in the 150ml frozen water, with 1M NaOH solution regulator solution pH to 7.Ethyl acetate extraction, drying is removed on the Rotary Evaporators and is desolvated.Column chromatography purification (leacheate: toluene: sherwood oil=8: 5), obtain light yellow product 1.20g (productive rate 72.7%).
IR(KBr，cm
-1)：2824，2727，1688，893，802，765，751，697。
1H-NMR(CDCl
3，500MHz)：δ10.12(s，1H)，8.68(d，J＝0.9Hz，1H)，8.21(d，J＝7.8Hz，1H)，7.95(q，J＝1.5Hz，1H)，7.65(t，J＝7.8Hz，2H)，7.54(q，7.3Hz，3H)，7.50-7.43(m，2H)，7.39(q，J＝8.1Hz，2H)。
Embodiment 4, the preparation of PNCa-2CN: add 2.6ml (17.4mmol) isophorone and 1.1g (16.6mmol) propane dinitrile in 50ml eggplant type bottle.0.08ml glacial acetic acid and 0.06ml aceticanhydride are dissolved in 10ml DMF, get 2.4ml and add reaction flask, the 0.44ml piperidines is dissolved in 5ml DMF, get 2.4ml and add reaction flask, stirring at room 1 hour, being warming up to 80 ℃ again stirred 1 hour, add 1.10g (4.1mmol) 3-carboxaldehyde radicals-N-phenyl-carbazole, continue to stir 1 hour, pour into while hot in the 200ml hot water of (containing the dense HCl of 6ml), collect and separate out solid, crude product stirs in 80ml Virahol and 10ml water, suction filtration is collected solid, and the acetonitrile recrystallization gets red product 1.20g (productive rate 66.5%).
IR(KBr，cm
-1)：2958，2213，1390，893，801，763，750，700。
H-NMR(CDCl
3，500MHz)：δ8.29(s，1H)，8.16(d，J＝7.7Hz，2H)，7.65-7.51(m，6H)，7.45-7.26(m，5H)，7.08(d，J＝11.0Hz，1H)，6.87(s，1H)，2.62(s，2H)，2.54(s，2H)，1.11(s，6H)。
Solid photoluminescence (film, excitation wavelength 405nm): peak wavelength 660nm, peak width at half height 138nm;
Chromaticity coordinates: x=0.533, y=0.384.
MS(EI)：m/e?441(M
+)。
Ultimate analysis: calculated value (C
31H
25N
3): C, 84.74; H, 5.69; N, 9.57.Measured value: C, 85.01, H, 5.81; N, 9.64.
Embodiment 5,3, the preparation of 6-diformazan aldehyde radical-N-phenyl-carbazole: add 2.50g (10.3mmol) N-phenyl carbazole, 19.9ml (0.26mol) DMF and 20ml 1 in the 250ml eggplant-shape bottle, the 2-ethylene dichloride.Reaction flask places ice-water bath, stirs to drip 23.9ml (0.26mol) POCl down
3Finish, in 95 ℃ of oil baths, refluxed 22 hours, pour into while hot in the 400ml frozen water, with 1M NaOH solution regulator solution pH to 7.Ethyl acetate extraction, drying is removed on the Rotary Evaporators and is desolvated.Column chromatography purification (leacheate: ethyl acetate: sherwood oil=1: 2), obtain yellow product 0.52g (productive rate 16.5%).
IR(KBr，cm
-1)：2820，2720，1686，900，813，761，698。
H-NMR(CDCl
3，500MHz)：δ10.16(s，2H)，8.74(s，2H)，8.03(q，J＝8.5Hz，2H)，7.69(t，J＝7.7Hz，2H)，7.61(q，J＝9.1Hz，1H)，7.55(d，J＝7.4Hz，2H)，7.47(d，J＝8.5Hz，2H)。
Embodiment 6, the preparation of PNCa-4CN: add 2.0ml (13.4mmol) isophorone and 0.9g (13.6mmol) propane dinitrile in 25ml eggplant type bottle.0.08ml glacial acetic acid and 0.06ml aceticanhydride are dissolved in 10ml DMF, get 1.9ml and add reaction flask, the 0.44ml piperidines is dissolved in 5ml DMF, get 1.9ml and add reaction flask, stirring at room 1 hour, being warming up to 80 ℃ again stirred 1 hour, add 0.52g (1.7mmol) 3,6-diformazan aldehyde radical-N-phenyl-carbazole continues to stir 2 hours, pour into while hot in the 100ml hot water of (containing the dense HCl of 3ml), solid is separated out in collection, and crude product stirs in 50ml Virahol and 8ml water, and suction filtration is collected solid, the acetonitrile recrystallization gets red product 0.60g (productive rate 55.6%).
IR(KBr，cm
-1)：2953，2222，1388，898，816，758，698。
1H-NMR(CDCl
3，500MHz)：δ8.32(s，2H)，7.65(q，J＝8.3Hz，4H)，7.56(t，J＝7.5Hz，4H)，7.40(d，J＝8.6Hz，2H)，7.33(d，J＝17.0Hz，1H)，7.09(d，J＝16.0Hz，2H)，6.89(s，2H)，2.63(s，4H)，2.54(s，4H)，1.12(s，12H)。
Solid photoluminescence (film, excitation wavelength 405nm): peak wavelength 666nm, peak width at half height 132nm;
Chromaticity coordinates: x=0.611, y=0.351.
MS(MALDI)：m/e?635(M)。
Ultimate analysis: calculated value (C
44H
37N
5): C, 83.15; H, 5.83; N, 11.02.Measured value: C, 83.83; H, 5.58; , N, 10.72.
Embodiment 7, and the red organic electroluminescence device preparation: the ITO conductive glass puts into 1.0 * 10 after cleaning
-4In the vacuum chamber of Pa, evaporation 50nm NPB, 30nm mix up Alq3, the 50nmAlq3 of 5%PNCa-2CN successively, then in another vacuum chamber (1.0 * 10
-4Pa) evaporation 50nm magnesium silver alloys and argent electrode, obtaining structure is the device of ITO/NPB/Alq3:PNCa-2CN (5%)/Alq3/Mg:Ag/Ag, and the device un-encapsulated is measured in nitrogen atmosphere, and playing bright voltage is 5V (1cd/m
2), high-high brightness is 2372cd/m
2, maximum luminous power 1.25lm/W.
Claims (5)
1. the red organic electrofluorescence material based on the N-aryl carbazole is characterized in that having the basic structure of N-aryl carbazole, contains a plurality of identical chromophoric groups in a part---the many nitriles of conjugation, and structure is as follows:
Wherein, Ar is a phenyl or naphthyl, and the n value is 0 or 1.
2. the preparation method of red organic electrofluorescence material according to claim 1, it is characterized in that generating intermediate product in 0.5-2 hour by isophorone (I) and propane dinitrile (II) reaction, without separation, direct and N-aryl carbazole aldehyde derivatives (III) reaction obtained target molecule in 0.5-2 hour, the reactant molar ratio example is I: II: III=1: 1: 0.1-1, reaction medium is a glacial acetic acid, aceticanhydride, piperidines and DMF mixture, the mol ratio of mixed solvent is 2.5: 1 successively: (4-4.5): (450-500), temperature of reaction is 25-100 ℃
N=0,1, Ar such as claim 1 definition.
3. the preparation method of red organic electrofluorescence material according to claim 2 is characterized in that N-aryl carbazole aldehyde derivatives is to be got by the dimethyl formamide formylation reaction under Phosphorus Oxychloride by the N-aryl carbazole.
4. luminescent material according to claim 1 is used to make red organic electroluminescence device.
5. luminescent material according to claim 1 is used to make full-color organic electroluminescent devices.
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|---|---|---|---|---|
| JP2001115154A (en) * | 1999-10-22 | 2001-04-24 | Toppan Printing Co Ltd | Organic thin-film luminescent element and phosphor |
| US6528657B2 (en) * | 1999-12-02 | 2003-03-04 | Taiho Industries Co., Ltd. | Fluorescent carbazole derivative |
| JP2003292948A (en) * | 2002-04-05 | 2003-10-15 | Nichia Chem Ind Ltd | Red luminescent material and organic electroluminescent element using the same |
| CN1557906A (en) * | 2004-01-29 | 2004-12-29 | 复旦大学 | Red organic electroluminescent materials and method for preparing same |
| CN1594494A (en) * | 2004-07-05 | 2005-03-16 | 复旦大学 | Red organic electroluminescent materials containing naphthylamine group and method for preparing same |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001115154A (en) * | 1999-10-22 | 2001-04-24 | Toppan Printing Co Ltd | Organic thin-film luminescent element and phosphor |
| US6528657B2 (en) * | 1999-12-02 | 2003-03-04 | Taiho Industries Co., Ltd. | Fluorescent carbazole derivative |
| JP2003292948A (en) * | 2002-04-05 | 2003-10-15 | Nichia Chem Ind Ltd | Red luminescent material and organic electroluminescent element using the same |
| CN1557906A (en) * | 2004-01-29 | 2004-12-29 | 复旦大学 | Red organic electroluminescent materials and method for preparing same |
| CN1594494A (en) * | 2004-07-05 | 2005-03-16 | 复旦大学 | Red organic electroluminescent materials containing naphthylamine group and method for preparing same |
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