CN101126021A - Bi-vinyl anthracenes luminescent compounds - Google Patents
Bi-vinyl anthracenes luminescent compounds Download PDFInfo
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- CN101126021A CN101126021A CNA2007101641506A CN200710164150A CN101126021A CN 101126021 A CN101126021 A CN 101126021A CN A2007101641506 A CNA2007101641506 A CN A2007101641506A CN 200710164150 A CN200710164150 A CN 200710164150A CN 101126021 A CN101126021 A CN 101126021A
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- vinyl
- luminescent compounds
- anthracene
- thiophene
- anthracenes
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention discloses a luminescence compound of double-vinyl anthracene. The general structure formula is as follows: wherein, R1 is 2-thienyl or phenyl. The compound of the invention is mainly applied in organic electroluminescent displayer, can be directly used as a luminescence layer or used as a doping for making a luminescence layer function.
Description
Technical field
The present invention is a kind of bi-vinyl anthracenes compound, belongs to electroluminescent organic material, is mainly used in display of organic electroluminescence.
Background technology
To organism apply that voltage imports electric current and luminous phenomenon organic electroluminescent (OEL), this organism is called electroluminescent organic material, adopts the display device of this material making to claim display of organic electroluminescence (OLED).Luminescent material thin-film is added in the plate electrode intermediate fabrication and becomes panel display screen.
Luminescent material used in the display of organic electroluminescence divides polymer and small molecule material by type; Divide multiple materials such as blue light, green glow, ruddiness, gold-tinted, orange light by glow color.The anthracene compounds has higher quantum yield, still all has fluorescent effect preferably under the solid conditions in solution, is the good luminescent material of a class.European patent EP 1724852 discloses 9, and anthracene compound is as electroluminescent organic material for 10-two (2, the 2-diphenylethyllene), and structure is as follows:
9, two (2, the 2-diphenylethyllene) anthracenes of 10-
Substituting group on the compound vinyl in the above-mentioned patent only limits to phenyl, makes the kind of vinyl anthracenes luminescent compounds few.
Summary of the invention
Technical problem to be solved by this invention is to have overcome the deficiency that background technology exists, a kind of luminescent layer that is used alone as is provided, it is luminous also to can be used as adulterate body making luminescent layer, has expanded the bi-vinyl anthracenes luminescent compounds of the organic compound species that can prepare organic electroluminescence device.
In order to realize purpose of the present invention, the thienyl group that will contain sulphur atom is introduced in the vinyl anthracene, increases molecule lone-pair electron quantity, has strengthened " n-π
*" probability of transition of electron, the transition of electron of molecule and photoluminescent band kind are increased.
Bi-vinyl anthracenes luminescent compounds structural formula general formula of the present invention is as follows:
R wherein
1Be 2-thienyl or phenyl.
The preferred compound of the present invention, its structural formula is as follows:
R wherein
1Be the 2-thienyl.
Another preferred vinyl anthracenes luminescent compounds of the present invention, its structural formula is as follows:
R wherein
1Be phenyl.
The present invention can also synthesize a series of derivative, and its structural formula is as follows:
R
1Can be the alkyl that contains 1-6 carbon atom, can be contain alkyl that the aryl of 7-8 carbon atom replaces, can be the aryl, the cyclohexyl that contain 6-18 carbon atom, can be the alkoxyl group that contains the aryloxy of 6-18 carbon atom and contain 1-6 carbon atom.
R
2Can be one or more substituting groups, comprise the alkyl of hydrogen, cyano group, halogenic substituent, nitro, amido, a 1-6 C, the aroyl of the aralkyl of the alkoxyl group of 1-6 carbon, a 7-8 carbon, the ester acyl group of a 1-3 carbon, a 7-10 carbon etc.
And, R
1, R
2In said aryl, cyclohexyl, aryloxy can have various R
2Substituting group.
Advantage of the present invention is as follows:
The present invention has increased the kind of vinyl anthracenes luminescent compounds, and melting point compound height of the present invention, and fusing point can reach 310.2 ℃ (DSC), Heat stability is good.
Embodiment
Embodiment 1:9,10-two [2, two (2-thiophene) the basic vinyl of 2-] anthracenes synthetic
1.1 the present invention implements with reference to following synthetic route
1.2 9,10-two [2, two (2-thiophene) the basic vinyl of 2-] anthracenes synthetic
1.2.1 raw material is synthetic
The present invention used 9, disclosed method is synthetic in two (di ethoxy phosphoryl methyl) anthracene reference literatures [functional materials, 2004,5 (35): 595-597] of 10-; Two thienyl ketone reference literature [Organic syntheses Coll.Vol.2,520; Vol.12,62] disclosed method is synthetic in.
1.2.2 product is synthetic
In the 250ml four-hole bottle, add 9, two (di ethoxy phosphoryl methyl) anthracene 9.8g of 10-, sodium hydride 5.1g, two (2-thiophene) basic ketone 8.5g, tetrahydrofuran (THF) 100ml begins to stir, and heat temperature raising is to refluxing.Behind the back flow reaction 4h, stopped reaction naturally cools to room temperature under stirring, and is poured in the frozen water and stirs, and separates out a large amount of solids.Filter, with solid methanol wash 3 times, obtain product 9 then, 10-two [2, two (2-thiophene) the basic vinyl of 2-] anthracene 5.6g.At 230 ℃, 3 * 10
-3The Pa distillation is elevated product 4.5g.Fusing point: 310.2 ℃ (DSC).
Structure is identified:
Ultimate analysis: C
34H
22S
4
Theoretical value: C73.08%, H3.97%, S22.95%;
Measured value: C73.06%, H3.98%, S22.86%.
Infrared spectra (KBr, cm
-1): 3059,977 (C=C-H); 1618 (C=C); 1512,1435,1379,1343,761 (anthracene nucleus); 1042,842,707 (thiophene).
Magnetic resonance spectroscopy (
1H-NMR, CDCl
3, 500MHz): δ 6.931 (S, 2H); δ 7.126-7.144 (m, 4H);
δ7.359-7.391(m，8H)；δ8.205-8.225(m，8H)；
Confirm that the resulting material of above-mentioned reaction is 9 really, 10-two [2, two (2-thiophene) the basic vinyl of 2-] anthracene.
1.3 optical performance test
With 9,10-two [2, two (2-thiophene) the basic vinyl of 2-] anthracene is dissolved in methylene dichloride, is mixed with dilute solution and measures its uv-visible absorption spectra and fluorescence spectrum.Uv-visible absorption spectra uses UNICO UV-2102PCS type ultraviolet-visible pectrophotometer to measure; Fluorescence spectrum 970CRT type fluorescent spectrophotometer assay.
Solution state absorption spectrum peak wavelength is 414nm; The fluorescence spectrum peak wavelength is 521nm.
Embodiment 2:9, two [2-(2-thiophene) base-2-phenyl vinyl] anthracenes of 10-synthetic
2.1 the present invention implements with reference to following synthetic route
2.2 9, two [2-(2-thiophene) base-2-phenyl vinyl] anthracenes of 10-synthetic
2.2.1 raw material is synthetic
The present invention used 9, disclosed method is synthetic in two (diethoxy phosphinylidyne methylene radical) the anthracene reference literatures [functional materials, 2004,5 (35): 595-597] of 10-; Thienyl benzophenone reference literature [Organic syntheses Coll.Vol.2,520; Vol.12,62] disclosed method is synthetic in.
2.2.2 product is synthetic
In the 250ml four-hole bottle, add 9, two (diethoxy phosphinylidyne methylene radical) the anthracene 9g of 10-, sodium hydride 5g, 2-thienyl benzophenone 8.3g, tetrahydrofuran (THF) 100ml begins to stir, heat temperature raising is to refluxing, behind the back flow reaction 4h, stopped reaction naturally cools to room temperature under stirring, be poured in the frozen water and stir, separate out a large amount of solids.Filter, with solid methanol wash 3 times, obtain product 9 then, two [2-(2-thiophene) base-2-phenyl vinyl] the anthracene 6.4g of 10-.At 220 ℃, 3 * 10
-3The Pa distillation is elevated product 5.5g.Fusing point: 277.8 ℃ (DSC).
Structure is identified:
Ultimate analysis: C
38H
26S
2
Theoretical value: C83.48%, H4.79%, S11.73%;
Measured value: C83.46%, H4.80%, S11.69%.
Infrared spectra: 3078 (C=C-H); 1619 (C=C); 1593,1516,1490,1437,1378,775 (anthracene nucleus); 1041 (thiophene); 756,697 (single-substituted).
Magnetic resonance spectroscopy: δ 6.564-6.599 (m, 2H); δ 6.862-6.933 (m, 4H); δ 7.015 (S, 2H); δ 7.045-7.085 (m, 2H); δ 7.293-7.407 (m, 6H); δ 7.430-7.520 (m, 4H); δ 7.696-7.715 (m, 2H); δ 8.184 (d, 2H); δ 8.298 (d, 2H).
Confirm that the resulting material of above-mentioned reaction is 9 really, two [2-(2-thiophene) base-2-phenyl vinyl] anthracenes of 10-.
2.3 optical performance test
With 9, two [2-(2-thiophene) base-2-phenyl vinyl] anthracenes of 10-are dissolved in methylene dichloride, are mixed with dilute solution and measure its uv-visible absorption spectra and fluorescence spectrum.Uv-visible absorption spectra uses UNICO UV-2102PCS type ultraviolet-visible pectrophotometer to measure; Fluorescence spectrum 970CRT type fluorescent spectrophotometer assay.
Solution state absorption spectrum peak wavelength is 411nm, and the fluorescence spectrum peak wavelength is 494nm.
Claims (3)
1. bi-vinyl anthracenes luminescent compounds, the structural formula general formula is as follows:
R wherein
1Be 2-thienyl or phenyl.
2. bi-vinyl anthracenes luminescent compounds according to claim 1 is characterized in that structural formula is as follows:
R wherein
1Be the 2-thienyl.
3. bi-vinyl anthracenes luminescent compounds according to claim 1 is characterized in that structural formula is as follows:
R wherein
1Be phenyl.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007101641506A CN101126021A (en) | 2007-10-08 | 2007-10-08 | Bi-vinyl anthracenes luminescent compounds |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007101641506A CN101126021A (en) | 2007-10-08 | 2007-10-08 | Bi-vinyl anthracenes luminescent compounds |
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| Publication Number | Publication Date |
|---|---|
| CN101126021A true CN101126021A (en) | 2008-02-20 |
Family
ID=39094160
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2007101641506A Pending CN101126021A (en) | 2007-10-08 | 2007-10-08 | Bi-vinyl anthracenes luminescent compounds |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101875717A (en) * | 2010-07-20 | 2010-11-03 | 中南大学 | Copolymer of bithiophene diazosulfide and dibenzothiophene (BDT) and application thereof |
| CN101935389A (en) * | 2010-07-20 | 2011-01-05 | 中南大学 | 2-thiophene-benzotriazole-based polymer materials and photovoltaic application thereof |
-
2007
- 2007-10-08 CN CNA2007101641506A patent/CN101126021A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101875717A (en) * | 2010-07-20 | 2010-11-03 | 中南大学 | Copolymer of bithiophene diazosulfide and dibenzothiophene (BDT) and application thereof |
| CN101935389A (en) * | 2010-07-20 | 2011-01-05 | 中南大学 | 2-thiophene-benzotriazole-based polymer materials and photovoltaic application thereof |
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| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
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Open date: 20080220 |