CN1687035A - Derivative of 8-hydroxyquinoline of emitting red light - Google Patents
Derivative of 8-hydroxyquinoline of emitting red light Download PDFInfo
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- CN1687035A CN1687035A CN 200510025045 CN200510025045A CN1687035A CN 1687035 A CN1687035 A CN 1687035A CN 200510025045 CN200510025045 CN 200510025045 CN 200510025045 A CN200510025045 A CN 200510025045A CN 1687035 A CN1687035 A CN 1687035A
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Abstract
The present invention relates to a 8-hydroxyquinoline derivative containing dicyanomethylisophorous. Said invention is characterized by adopting the following steps: chemically modifying 8-hydroxyquinoline, introducing the structure containing dicyanomethylisophorone and utilizing the group capable of forming conjugated system or the group capable of introducing N atoms as donor group to form conjugated system with D-pi-A structure to form connection between two functional gruops of hydroxyquinolnie and dicyanomethylisopho-rone. The dicyan and 8-hydroxyquinoline metal complex in said compound can effectively reduce molecular LUMO track, raise electronic transmission performance of material, so that it is a n-type semiconductor material emitting red light.
Description
Technical field
The present invention relates to a kind of oxine derivative, specifically, relate to a kind of oxine derivative that contains dicyanogen methyl isophorone.
Background technology
Along with Development of Multimedia Technology, more and more higher to the performance requriements of flat-panel monitor.Organic electroluminescence device (OLED) has low-voltage DC driving, active illuminating, vision is big, response speed is fast, rich color and low cost and other advantages, is acknowledged as the technique of display of future generation of the most desirable and tool development prospect.Since 2000, the whole world has started OLED research and development upsurge, and prototype hardware and product are constantly released, and average annual rate of growth has surpassed 100%, 2003 year world's OLED sales revenue and reached 2.63 hundred million dollars, increases by 127% than the last year.By 2008, OLED industry in the world will keep the compound growth rate more than 60% from now in Display Search prediction.
Luminous organic material is an integral part crucial in the organic electroluminescence device, selects different organic materialss for use, just can obtain various color.Luminescent layer can be divided into two classes basically, i.e. host emitter and guest emitter.Host emitter itself has the character that transmission electronic or transporting holes or both have, usually use with transmission charge layer one time-out, in the hope of allow positive and negative charge in conjunction with the exciton that is produced can be limited in organic layer at the interface and luminous.Guest emitter in use needs to be dispersed in the material of main part, accepts the energy from the material of main part that is excited, and produces distinct colors through transmission ofenergy.
Oxine aluminium (Alq
3) by the electric transmission body and the luminescent material of widespread use.1987, Tang (Appl.Phys.Lett., 1987,51,913) oxine aluminium (Alq
3) as luminescent material, aromatic diamines type compound has prepared the double-deck organic electroluminescence device of sandwich-like as hole mobile material, driving voltage is less than 10V, and luminosity is greater than 1000cd/m
2, external quantum efficiency surpasses 1%, is obtaining important breakthrough aspect the Organic Light Emitting Diode research.Studies show that in a large number, by mixing, change Alq
3Crystal formation or use different parts can adjust Alq
3Luminescent properties.
From present research, efficient blue and green luminescent material can satisfy the needs of practicability, and still there are problems such as luminous efficiency and luminosity be lower in red illuminating material, and the kind of red illuminating material is fewer, thereby continues red illuminating material research is very important.Red illuminating material relatively more commonly used at present is 4-methylene dicyanoethyl-2-methyl-6-(p-dimethylamino styryl)-4H-pyrans (DCM) and 4-methylene dicyanoethyl-2-methyl-6-(1,1,7,7-tetramethyl-julolidine-9-yl)-4H-pyrans (DCJTB), they are entrained in Alq usually
3In as luminescent layer, and Alq
3As electron transfer layer.Because DCM and these two kinds of dyestuffs of DCJTB are two dimensional structure, form state of aggregation easily, have very obviously by the self-quenching phenomenon that doping content caused, very big to the luminescent properties influence of device, luminescent chromaticity and brightness are difficult to take into account.
Summary of the invention
The present invention is by carrying out chemically modified to oxine: introduce the structure that contains dicyanogen methyl isophorone, and make between two kinds of functional groups of hydroxyquinoline and dicyanogen methyl isophorone to couple together as the group that electron-donating group forms the conjugated system of D-π-A structure, obtain the compound of the rubescent look fluorescence of a class by the group or the introducing N atom that can form conjugated system.Utilize oxine and performance metal complex in this compounds, make organic electroluminescent metal complex material.Not only can bring into play the electron transport property of metal complex, can take into account the performance of red main body luminescent material simultaneously again.Can avoid because the self-quenching phenomenon that the very significant concn that the two dimensional structure of DCM and two kinds of dyestuffs of DCJTB is brought is mixed and caused.
The said oxine derivative of the present invention is characterized in that, said derivative is following compounds I or is the metal complex of part with the Compound I,
Wherein: R is hydrogen, C
1～C
18Alkyl or C
1～C
18Alkoxyl group; L is for forming the group of all or part of conjugated system with quinoline or dicyan methyne tetrahydrobenzene.
Preferred in the present invention metal complex is following compounds II
In Compound I or Compound I I: preferred R is hydrogen, C
1～C
6Alkyl or C
1～C
6Alkoxyl group, preferred R are hydrogen, methyl, ethyl or sec.-propyl; Preferred L be vinyl (CH=CH-), ethynyl (C ≡ C-) or-R
1-Ar-CH=CH-, wherein R
1Be CH=CH, C=C, C=N or sulfoamido, Ar is C
6～C
44Aromatic nucleus or aromatic amine, preferred Ar is aromatic nucleus or the aromatic amine with following structure:
Best Ar is a benzene.
The said oxine derivative of the present invention can synthesize as follows:
2-(3,5, the 5-3-methyl cyclohexanol is rare-2-subunit) propane dinitrile reacts in solvent with corresponding oxine formaldehyde and directly obtains compound (I); Perhaps by 2-(3,5, the 5-3-methyl cyclohexanol is rare-the 2-subunit) and propane dinitrile and corresponding aldehyde (as: paranitrobenzaldehyde or to piperazinyl phenyl formaldehyde etc., said aldehyde compound can be commercially available product or adopt prior art to make) compound that obtains of reaction, be connected with oxine again and obtain compound (I).
Compound (I) and aluminum chloride, triethyl aluminum, aluminum ethylate or aluminum isopropylate etc. are carried out complexing in organic solvent, after purifying, obtain compound (II).
The said oxine derivative of the present invention is by the group that can form conjugated system or introduces nitrogen-atoms forms the conjugated system of D-π-A structure as electron-donating group group connection quinoline and two kinds of functional groups of dicyanogen methyl isophorone, dicyanogen methyl isophorone in this compounds and oxine metal complex can effectively reduce the LUMO track of molecule, the electronic transmission performance of raising material, are the n N-type semiconductorN materials that glows that a class has application prospect very much.
Embodiment
The present invention is further elaborated below by embodiment, and its purpose is better to understand content of the present invention.Therefore, the cited case should not be considered as limiting the scope of the invention.
Embodiment 1
Synthesizing of Compound I-1:
In flask, add 0.346 gram 5-formyl radical-oxine (2mmol), 0.372 gram 2-(3,5, the 5-3-methyl cyclohexanol is rare-the 2-subunit) propane dinitrile (2mmol), new anhydrous acetonitrile and 2 piperidines handled of 5ml.Under argon shield, reaction mixture refluxed 20h.Separate out the scarlet precipitation behind the reactant cool to room temperature, filter, with the washing of 10ml acetonitrile.Drying gets scarlet powder 0.612 gram, productive rate 92.8%.
m.p.253～255℃。
1H?NMR(500MHz，CDCl
3，ppm)：δ8.91(d，J＝3.5Hz，1H)，8.66(d，J＝7.5Hz，1H)，7.91(d，J＝6.2Hz，1H)，7.68(s，1H)，7.65(t，J＝5.5Hz，1H)，7.40(m，1H)，7.05(d，1H)，6.9(s，1H)，2.64(s，2H)，2.57(s，2H)，1.13(s，6H)。
Maximum absorption wavelength in tetrahydrofuran (THF) is 437nm (log ε=4.25), and maximum emission wavelength is 603nm, is fluorescent red-orange.
Embodiment 2
Synthesizing of Compound I-2:
(1) (E)-2-(3-(4-nitrostyrolene base)-5,5-dimethyl hexamethylene-2-thiazolinyl) propane dinitrile (compd A) synthetic:
In flask, add 0.66 gram paranitrobenzaldehyde (4.4mmol), 0.81 gram 2-(3,5, the 5-3-methyl cyclohexanol is rare-the 2-subunit) propane dinitrile (4.4mmol), new anhydrous acetonitrile and 2 piperidines handled of 5ml.Under the argon shield, backflow 2h.Separate out pale brown look precipitation behind the reactant cool to room temperature, filter, with the washing of 10ml acetonitrile.Drying gets the pale brown toner of compd A end 1.05 grams, productive rate 72.0%.
(2) (E)-2-(3-(4-amino-benzene vinyl)-5,5-dimethyl hexamethylene-2-thiazolinyl) propane dinitrile (compd B) synthetic:
In flask, add 1.05 and digest compound A (3.3mmol), 3.70 grams, two hydration dichloros inferior tin (16.4mmol), 20ml ethanol and 2 Glacial acetic acid.Under the argon shield, backflow 2.5h.After under argon shield, being cooled to room temperature, pour in the 50ml water, with 3 * 50ml ethyl acetate extraction.Merge organic phase, behind anhydrous magnesium sulfate drying, revolve steam the red-brown powder.Cross silicagel column with sherwood oil/methylene dichloride (1: 4) developping agent, get compd B, red powder 0.79 gram, productive rate: 83.0%.
(3) Compound I-2 is synthetic
In flask, add 0.23 and digest compound B (0.8mmol), 0.14 gram 5-aldehyde radical-oxine (0.8mmol) and 10ml dehydrated alcohol.Under argon shield, back flow reaction 20h separates out red solid after leaving standstill cooling, filters, and thick product obtains Compound I-2, red powder 0.24g, productive rate 69.7% with the dehydrated alcohol recrystallization.
m.p.234～236℃。
1H?NMR(500MHz，CDCl
3，ppm)：δ9.95(d×d，J＝1.22Hz，J＝1.30Hz，1H)，8.87(d×d，J＝1.32Hz，J＝1.36Hz，1H)，8.78(s，1H)，7.89(d，J＝11.68Hz，1H)，7.64(t，1H)，7.59(d，J＝8.40Hz，2H)，7.30(d，J＝8.33Hz，2H)，7.25(d， J＝2.80Hz，1H)，7.12～6.99(s，2H)，6.86(s，1H)，2.62～2.50(s，4H)，1.10(s，6H)。
Maximum absorption wavelength in tetrahydrofuran (THF) is 436nm (log ε=4.58), and maximum emission wavelength is 608nm, is fluorescent red-orange.
Embodiment 3
Synthesizing of Compound I-3
(1) the preparation reference of 8-hydroxy-2-methylquinoline-5-SULPHURYL CHLORIDE (J.A.C.S.2001,123,5160) is to the synthesized reference document (Dyes and Pigments 2003,59,143) of piperazinyl phenyl formaldehyde.
(2) Compound C is synthetic
In flask, add 0.19 gram to piperazinyl phenyl formaldehyde (1.0mmol), 0.20 gram salt of wormwood (1.5mmol) and 20ml methylene dichloride behind the stirring 20min, adds 0.26 gram 8-hydroxy-2-methylquinoline-5-SULPHURYL CHLORIDE (1.0mmol), stirring at room 4h in batches.Pour in the 50ml water, use dichloromethane extraction, the organic phase anhydrous sodium sulfate drying.Get chocolate brown powder after revolving steaming, cross silicagel column with the developping agent of chloroform/methanol (4: 1).Collect first component, revolve light-colored powder 0.32 gram after the steaming.Productive rate 77.8%.
(3) Compound I-3 is synthetic
In flask, add 84 milligrams of Compound C (0.2mmol), 38 milligrams of 2-(3,5, the 5-3-methyl cyclohexanol is rare-the 2-subunit) propane dinitrile (0.2mmol), new anhydrous acetonitrile and 2 piperidines handled of 3ml.Under the argon shield, backflow 5h.Separate out the scarlet precipitation behind the reactant cool to room temperature, filter, with the washing of 5ml acetonitrile.Drying gets 73 milligrams in scarlet powder, productive rate 61.7%.
m.p.222～224℃。
1H?NMR(500MHz，CDCl
3，ppm)：δ8.96(d，J＝8.9Hz，1H)，8.14(d，J＝8.2Hz，1H)，7.49(d，J＝8.8Hz，1H)，7.38(d，J＝8.7Hz，1H)，7.22(d，J＝14.1Hz，1H)，7.12(d，J＝6.1Hz，1H)，6.96(d，1H)，6.84～6.72(m，4H)，3.25(b，8H)，2.76(s，3H)，2.48～2.10(s，4H)，1.06～0.92(s，6H)。
MS-ESI?m/e：602.2(100％)[M
++Na]，618.2(48.20％)[M
++K].
Maximum absorption wavelength in tetrahydrofuran (THF) is 451nm (log ε=4.32), and maximum emission wavelength is 630nm, is red fluorescence.
Embodiment 4
Compound I I-1's is synthetic:
In flask, add 34 milligrams of Compound I-1, the 20ml dry toluene under the argon shield, is heated to backflow.The 2ml anhydrous toluene solution that adds 6.8 milligrams of aluminum isopropylates.Backflow 6h.After the cooling, there is red solid to separate out.Solution is spin-dried for, gets 33 milligrams in purplish red powder.
1H?NMR(500MHz，CDCl
3，ppm)：δ8.85(d，J＝4.1Hz，1H)，8.53(d，J＝8.7Hz，1H)，7.87(d，J＝8.2Hz，1H)，7.67(d，J＝5.7Hz，1H)，7.58(t，J＝5.5Hz，1H)，7.24(m，1H)，7.05(d，J＝5.7Hz，1H)，6.89(s，1H)，2.64(s，2H)，2.57(s，2H)，1.13(s，6H)。
Maximum absorption wavelength in tetrahydrofuran (THF) is 444nm (log ε=4.86), and maximum emission wavelength is 603nm, is fluorescent red-orange.
Embodiment 5
Compound I I-2's is synthetic
Method according to synthetic compound II-1 is carried out, and uses Compound I-2 to be raw material, and the reaction times is 8h.Can obtain the target product red powder.
1H?NMR(500MHz，CDCl
3，ppm)：δ9.95(d，J＝8.5Hz，1H)，8.87(d，J＝4.0Hz，1H)，8.78(s，1H)，7.90(d，J＝8.1Hz，1H)，7.64(t，1H)，7.59(d，J＝8.40Hz，2H)，7.30(d，J＝8.33Hz，2H)，7.25(d，J＝2.80Hz，1H)，7.12～6.99(s，2H)，6.86(s，1H)，2.62～2.50(s，4H)，1.10(s，6H)。
Maximum absorption wavelength in tetrahydrofuran (THF) is 436nm (log ε=4.92), and maximum emission wavelength is 608nm, is fluorescent red-orange.
Embodiment 6
Compound I I-3's is synthetic
Method according to synthetic compound II-1 is carried out, and uses Compound I-3 to be raw material, replaces aluminum isopropylate with aluminium triethyl, uses the exsiccant tetrahydrofuran (THF) as solvent, stirring at room 2 days.Be spin-dried for solvent and can obtain the target product red powder.
1H?NMR(500MHz，CDCl
3，ppm)：δ?8.96(d，J＝8.9Hz，1H)，8.14(d，J＝8.2Hz，1H)，7.49(d，J＝8.8Hz，1H)，7.38(d，J＝8.7Hz，1H)，7.22(d，J＝14.1Hz，1H)，7.12(d，J＝6.1Hz，1H)，6.96(d，1H)，6.84～6.72(m，4H)，3.25(b，8H)，2.76(s，3H)，2.48～2.10(s，4H)，1.06～0.92(s，6H)。
Maximum absorption wavelength in tetrahydrofuran (THF) is 451nm (log ε=4.28), and maximum emission wavelength is 630nm, is red fluorescence.
Claims (5)
1, a kind of oxine derivative is characterized in that, said derivative is following compounds I or is the metal complex of part with the Compound I,
Wherein: R is hydrogen, C
1～C
18Alkyl or C
1～C
18Alkoxyl group; L is for forming the group of all or part of conjugated system with quinoline or dicyan methyne tetrahydrobenzene.
2, derivative as claimed in claim 1 is characterized in that, wherein said metal complex is following compounds II
Wherein: R is hydrogen, C
1～C
18Alkyl or C
1～C
18Alkoxyl group; L is for forming the group of all or part of conjugated system with quinoline or dicyan methyne tetrahydrobenzene.
3, derivative as claimed in claim 1 or 2 is characterized in that, wherein R is hydrogen, C
1～C
6Alkyl or C
1～C
6Alkoxyl group; Ar is C
6～C
44Aromatic nucleus or aromatic amine; L is-CH=CH-,-C=C-or-R
1-Ar-CH=CH-; R wherein
1Be CH=CH, C=C, C=N or sulfoamido.
4, derivative as claimed in claim 3 is characterized in that, wherein R is hydrogen, methyl, ethyl or sec.-propyl; Ar is a following compounds
5, derivative as claimed in claim 4 is characterized in that, described derivative is Compound I-1, Compound I-2, Compound I-3, Compound I I-1, Compound I I-2 or Compound I I-3.
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