CN102329264A - Preparation and application of organic white light emitting material L-Cl - Google Patents
Preparation and application of organic white light emitting material L-Cl Download PDFInfo
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- CN102329264A CN102329264A CN201110176854A CN201110176854A CN102329264A CN 102329264 A CN102329264 A CN 102329264A CN 201110176854 A CN201110176854 A CN 201110176854A CN 201110176854 A CN201110176854 A CN 201110176854A CN 102329264 A CN102329264 A CN 102329264A
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract
The invention belongs to the technical fields of light emission and display and relates to preparation and application of an organic white light emitting material L-Cl. The chemical formula of the material is as follows: [C27H20N4Cl].ClO4, wherein the main body of the chemical formula is 4'-(N-(4-chloro-benzal)-4-pyridyl-2,2':6'2''-terpyridinium, the other part of the chemical formula is an balanced anion ClO4<-1> which can be replaced by Cl<-1>, NO3<-1>, PF6<-1>, BF4<-1> and the like, and the molecular weight of L-Cl is 535.37. According to the invention, the organic white light emitting material L-Cl can be prepared by using a nucleophilic substitution method; and the dual emission of the crystal or film of the material exists in the range of 400-750nm, the material can emit while light under the excitation of an ultraviolet lamp of 365nm. According to the invention, the defects that organic multi-molecule mixed material is poor in stability, easily generates phase separation, needs high preparation process and the like are improved through using the material provided by the invention; and the material provided by the invention can be used for preparation of while light LED (light-emitting diode) and other light-emitting display fields.
Description
Technical field
The present invention relates to white organic emissive material 4 '-(N-(4-chloro-Ben Yajiaji)-4-pyridyl)-2,2 ': 6 ', 2 ' '-preparation and the application of terpyridyl salt L-Cl.
Background technology
The design of white organic emissive material is the focus of OLED material development with synthesizing in recent years always.Because to have stability not high for the organopolysiloxane mixing material, be separated easily and need shortcoming such as higher preparation technology, the research and development of stable organic supramolecular white fluorescent material receive publicity day by day.Yet because white light is complex light, normally by redness, yellow, blue three primary colors or blue light mix formation mutually with gold-tinted, so it is very rare up to the present to have an organic supramolecular of stable white fluorescence, and nearly all report all concentrates in the solution.As everyone knows, organic molecule in solid since its configuration and accumulation influence its fluorescence radiation character often with solution in different, so exploitation stable organic white fluorescent material in solid-state is most important.
At present, the most typical method of composite solid state white light organic molecule material is the exciplex strategy.Just utilize the organic molecule that self has blue-fluorescence to produce exciplex through accumulation, thereby in solid-state, produce the Two Colour Fluorescence emission, compound back produces white light.It is bigger that yet such long-wavelength fluorescence emission that produces is influenced by accumulation often, piles up the change of distance between the molecule and just can make moving even cancellation of growing wave emission wavelength, in reality is synthetic, is difficult to control.In order to overcome this shortcoming, we have synthesized a kind of novel molecules of salt, through the power of charge transfer effect in the regulatory molecule, have successfully realized the white light emission of one-component molecule.
Summary of the invention
The objective of the invention is to prepare a kind of white organic emissive material 4 '-(N-(4-chloro-Ben Yajiaji)-4-pyridyl)-2,2 ': 6 ', 2 ' '-terpyridyl salt, be abbreviated as L-Cl.
Its technical scheme is following:
We select 4 '-(4-pyridyl)-2; 2':6 ', 2 ' '-terpyridyl and 4-chlorobenzyl chloride are raw material, its mol ratio is about 1:2; Adopt DMF to make solvent; Through nucleophilic substitution reaction make monochlor(in)ate 4 '-(N-(4-chloro-Ben Yajiaji)-4-pyridyl)-2,2 ': 6 ', 2 ' '-terpyridyl (L-ClCl).Make L-ClClO through IX subsequently
4The main absorption of vibrations of its ir spectra is (KBr, cm as follows
– 1): 1641 (s), 1582 (s), 1545 (m), 1517 (m), 1495 (m), 1467 (m), 1392 (s), 1161 (m), 1089 (s), 1017 (w), 835 (w), 793 (s), 784 (s), 620 (s).
In addition, we also through X-ray single crystal diffraction technical measurement compound L-ClClO
4Structure, its structural parameter are following: molecular formula C
27H
20N
4Cl
2O
4, molecular weight 535.37, triclinic(crystalline)system, spacer P-1, unit cell parameters does
a=10.126 (11),
B=10.856 (13),
c=12.859 (14);
α=111.102 (14),
β=101.777 (13),
γ=96.192 (6) °, V=1265 (2)
3, Z=2.Its structural formula is following:
Fluorescence spectral measuring shows, L-ClClO
4Have good luminous property,, also have the intensity of a broad to be about the half the fluorescence emission peak of 441 nm emission peaks at 557 nm places except there is a strong fluorescent emission at 421 nm places.The bandwidth of whole fluorescent emission bands of a spectrum is 400-750 nm, almost comprises whole visible region.The tristimulus coordinates that obtains its fluorescent emission according to the criterion calculation of international lighting association (CIE) is (0.368,0.330), under the uv lamp of 365 nm, launches white fluorescent.
The material preparation method that the present invention adopted has that technology is simple, productive rate is high and advantage such as good stability.The preparation and other the luminous demonstration field that can be used for white light LEDs.Can be through IX, with ClO
4 –Balance anion is replaced into Cl
–, NO
3 –, PF
6 –, BF
4 –Deng luminescent properties regulated and control and being used for luminous and technique of display field.
Embodiment
1, the preparation of compound
With 0.3 g 4 '-(4-pyridyl)-2; 2':6 '; 2 ' '-terpyridyl molecule and 0.34 g 4-chlorobenzyl chloride be dissolved among the 8 mL DMF; Join then and be heated to 125 oC in the round-bottomed flask and react about 4 h,, obtain white powder product L-ClCl behind the filtering drying when the adularescent deposition generation of reaction solution cooling back.
Take by weighing 30 mg L-ClCl samples and 80 mg LiClO
4Be dissolved in the 3 mL zero(ppm) water; With 0.1 mol/L NaOH pH value of solution is adjusted to 7, after the stirring mixing solutions is joined in the stainless steel cauldron that contains polytetrafluoroethylliner liner, be heated to 110 oC constant temperature 3 days; In 3 days, reduce to room temperature afterwards, obtain colourless bulk crystals L-ClClO
4
2, performance test
We are to L-ClClO
4Crystal and PVP film have carried out fluorescence spectrum test test, under the excitation wavelength of 365 nm, are respectively (0.368,0.330) and (0.264,0.254) by the tristimulus coordinates of its fluorescent emission of criterion calculation of international lighting association (CIE), within the white light scope.
Claims (4)
1. white organic emissive material, this material be 4 '-(N-(4-chloro-Ben Yajiaji)-4-pyridyl)-2,2 ': 6 ', 2 ' '-terpyridyl salt, its molecular formula C
27H
20N
4Cl
2O
4, molecular weight 535.37, triclinic(crystalline)system, spacer P-1, unit cell parameters does
a=10.126 (11),
B=10.856 (13),
c=12.859 (14);
α=111.102 (14),
β=101.777 (13),
γ=96.192 (6) °, V=1265 (2)
3, Z=2, its structural formula is following:
2. the preparation method of the described white organic emissive material of claim 1 is characterized in that: select 4 '-(4-pyridyl)-2,2':6 '; 2 ' '-terpyridyl and 4-chlorobenzyl chloride are raw material; Its mol ratio is about 1:2, adopts DMF to make solvent, prepares through nucleophilic substitution reaction.
3. the purposes of the described white organic emissive material of claim 1 is characterized in that being used for luminous this material and the technique of display field.
4. the purposes of the described white organic emissive material of claim 1 is characterized in that through IX, with ClO
4 –Balance anion is replaced into Cl
–, NO
3 –, PF
6 –, BF
4 –Deng luminescent properties regulated and control and being used for luminous and technique of display field.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110176854.1A CN102329264B (en) | 2011-06-28 | 2011-06-28 | Preparation and application of organic white light emitting material L-Cl |
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| CN201110176854.1A CN102329264B (en) | 2011-06-28 | 2011-06-28 | Preparation and application of organic white light emitting material L-Cl |
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| CN102329264A true CN102329264A (en) | 2012-01-25 |
| CN102329264B CN102329264B (en) | 2015-03-04 |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002091493A2 (en) * | 2001-05-04 | 2002-11-14 | Elam-T Limited | Electroluminescent device |
| CN1407052A (en) * | 2001-08-22 | 2003-04-02 | 中国科学院大连化学物理研究所 | Rare earth fluorescent marker and its application |
| CN1811430A (en) * | 2005-01-26 | 2006-08-02 | 中国科学院大连化学物理研究所 | Singlet oxygen europium coordination compound fluorescent probe and application thereof |
| CN101544673A (en) * | 2009-04-24 | 2009-09-30 | 大连理工大学 | ECL marker of binuclear bipyridyl ruthenium/osmium connected by saturated carbon chains of different lengths |
| WO2010017260A1 (en) * | 2008-08-07 | 2010-02-11 | Merck & Co., Inc. | Tripyridyl carboxamide orexin receptor antagonists |
-
2011
- 2011-06-28 CN CN201110176854.1A patent/CN102329264B/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002091493A2 (en) * | 2001-05-04 | 2002-11-14 | Elam-T Limited | Electroluminescent device |
| CN1407052A (en) * | 2001-08-22 | 2003-04-02 | 中国科学院大连化学物理研究所 | Rare earth fluorescent marker and its application |
| CN1811430A (en) * | 2005-01-26 | 2006-08-02 | 中国科学院大连化学物理研究所 | Singlet oxygen europium coordination compound fluorescent probe and application thereof |
| WO2010017260A1 (en) * | 2008-08-07 | 2010-02-11 | Merck & Co., Inc. | Tripyridyl carboxamide orexin receptor antagonists |
| CN101544673A (en) * | 2009-04-24 | 2009-09-30 | 大连理工大学 | ECL marker of binuclear bipyridyl ruthenium/osmium connected by saturated carbon chains of different lengths |
Non-Patent Citations (1)
| Title |
|---|
| XU-HUI JIN ET AL.: "pH-induced coordination assembly of mononuclear and dinuclear copper(II) complexes based on a 4,4′-bipyridinium analogue", 《INORGANIC CHEMISTRY COMMUNICATIONS》, vol. 13, no. 1, 30 October 2009 (2009-10-30), pages 86 - 89, XP026820195 * |
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Granted publication date: 20150304 Termination date: 20190628 |