CN102329264B - 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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- CN102329264B CN102329264B CN201110176854.1A CN201110176854A CN102329264B CN 102329264 B CN102329264 B CN 102329264B CN 201110176854 A CN201110176854 A CN 201110176854A CN 102329264 B CN102329264 B CN 102329264B
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- pyridyl
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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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- Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
- Y02B20/00—Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps
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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-(the chloro-α-tolylene of 4-)-4-pyridyl)-2,2 ': 6 ', 2 ' ' the Synthesis and applications of-terpyridyl salt L-Cl.
Background technology
The Design and synthesis of white organic emissive material is the focus of OLED material research and development in recent years always.Due to organopolysiloxane mixing material, to have stability not high, and be easily separated and need the shortcomings such as higher preparation technology, the research and development of stable organic supramolecular white light phosphor receive publicity day by day.But due to white light be complex light, normally by redness, yellow, blue three primary colors or blue light are mixed to form mutually with gold-tinted, so the organic supramolecular up to the present with stable white fluorescence is very rare, and nearly all report is all concentrated in the solution.As everyone knows, organic molecule in solids due to its configuration and accumulation to affect its fluorescence radiation character often different from solution, so the organic white light phosphor stable in solid-state of exploitation is most important.
At present, the most typical method of composite solid state white light organic molecule material is exciplex strategy.Namely utilize the organic molecule self with blue-fluorescence to produce exciplex by accumulation, thus launch at solid-state middle generation Two Colour Fluorescence, after compound, produce white light.But such produced long-wavelength fluorescence transmitting often affects comparatively large by accumulation, the change of piling up distance between molecule just can make the movement even cancellation of growing wave emission wavelength, is difficult to control in reality synthesis.In order to overcome this shortcoming, we have synthesized a kind of novel molecules of salt, by the power of Charger transfer effect in regulatory molecule, successfully achieve the white light emission of one-component molecule.
Summary of the invention
The object of the invention is to prepare a kind of white organic emissive material 4 '-(N-(the chloro-α-tolylene of 4-)-4-pyridyl)-2,2 ': 6 ', 2 ' '-terpyridyl salt, be abbreviated as L-Cl.
Its technical scheme is as follows:
We select 4 '-(4-pyridyl)-2,2':6 ', 2 ' '-terpyridyl and 4-chlorobenzyl chloride are raw material, its mol ratio is about 1:2, DMF is adopted to make solvent, by nucleophilic substitution reaction obtain monochlor(in)ate 4 '-(N-(the chloro-α-tolylene of 4-)-4-pyridyl)-2,2 ': 6 ', 2 ' '-terpyridyl (L-ClCl).L-ClClO is obtained subsequently by ion-exchange
4.The principal vibration of its infrared spectra absorbs following (KBr, cm
– 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 pass through X-ray single crystal diffraction technical measurement compound L-ClClO
4structure, its structural parameter are as follows: molecular formula C
27h
20n
4cl
2o
4, molecular weight 535.37, triclinic(crystalline)system, spacer P-1, unit cell parameters is
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 as follows:
Fluorescence spectral measuring shows, L-ClClO
4there is good luminescent properties, except have a strong fluorescent emission at 421 nm places except, also have at 557 nm places a wider intensity to be about the fluorescence emission peak of 441 nm emission peak half.The bandwidth of whole fluorescent emission bands of a spectrum is 400-750 nm, almost comprises whole visible region.Obtain the tristimulus coordinates of its fluorescent emission according to the criterion calculation of international lighting association (CIE) for (0.368,0.330), under the ultraviolet lamp of 365 nm, launch white fluorescent.
Material preparation method of the present invention has that technique is simple, productive rate is high and the advantage such as good stability.Can be used for preparation and other luminescence display field of white light LEDs.By ion-exchange, by ClO
4 –balance anion is replaced into Cl
–, NO
3 –, PF
6 –, BF
4 –deng regulating and controlling luminescent properties and for luminous and technique of display field.
Embodiment
1, the preparation of compound
By 0.3 g 4 '-(4-pyridyl)-2,2':6 ', 2 ' '-terpyridyl molecule and 0.34 g 4-chlorobenzyl chloride are dissolved in 8 mL DMF, then join in round-bottomed flask and be heated to 125 oC reaction about 4 h, when adularescent precipitation produces after reaction solution cooling, after filtering drying, obtain white powder product L-ClCl.
Take 30 mg L-ClCl samples and 80 mg LiClO
4be dissolved in 3 mL distilled water, with 0.1 mol/L NaOH, pH value of solution is adjusted to 7, after stirring, mixing solutions is joined in the stainless steel cauldron containing polytetrafluoroethylliner liner, be heated to 110 oC constant temperature 3 days, in 3 days, be down 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, (0.368 is respectively by the tristimulus coordinates of its fluorescent emission of criterion calculation of international lighting association (CIE), 0.330) and (0.264,0.254), within white light range.
Claims (4)
1. a white organic emissive material, this material is 4 '-(N-(the chloro-α-tolylene of 4-)-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 is a=10.126 (11), b=10.856 (13),
α=111.102 (14), β=101.777 (13), γ=96.192 (6) °,
z=2, its structural formula is as follows:
2. the preparation method of a white organic emissive material according to claim 1, it is characterized in that: select 4 '-(4-pyridyl)-2,2':6 ', 2 "-terpyridyl and 4-chlorobenzyl chloride are raw material; its mol ratio is 1:2, adopt DMF to make solvent, obtain monochlor(in)ate 4 '-(N-(the chloro-α-tolylene of 4-)-4-pyridyl)-2; 2 ': 6 ', 2 "-terpyridyls by nucleophilic substitution reaction; Subsequently by ion-exchange obtained 4 '-"-terpyridyl salt, its molecular formula is C to (N-(the chloro-α-tolylene of 4-)-4-pyridyl)-2,2 ': 6 ', 2
27h
20n
4cl
2o
4.
3. a purposes for white organic emissive material according to claim 1, is characterized in that this material being used for luminous and technique of display field.
4. a purposes for white organic emissive material according to claim 1, is characterized in that by ion-exchange, by ClO
4 –balance anion is replaced into Cl
–, NO
3 –, PF
6 –, BF
4 –luminescent properties to be regulated and controled and for luminous and technique of display field.
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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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|---|---|---|---|
| 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 CN102329264A (en) | 2012-01-25 |
| CN102329264B true 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 |
|---|
| pH-induced coordination assembly of mononuclear and dinuclear copper(II) complexes based on a 4,4′-bipyridinium analogue;Xu-Hui Jin et al.;《Inorganic Chemistry Communications》;20091030;第13卷(第1期);第86-89页 * |
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