CN1321125C - Complexes of red light iridium by using nitrogen heterocycles in quinoline as ligand, and application - Google Patents
Complexes of red light iridium by using nitrogen heterocycles in quinoline as ligand, and application Download PDFInfo
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- CN1321125C CN1321125C CNB2005100167674A CN200510016767A CN1321125C CN 1321125 C CN1321125 C CN 1321125C CN B2005100167674 A CNB2005100167674 A CN B2005100167674A CN 200510016767 A CN200510016767 A CN 200510016767A CN 1321125 C CN1321125 C CN 1321125C
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- iridium
- red light
- alkyl
- quinoline
- alkoxyl group
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- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 15
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 15
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 239000003446 ligand Substances 0.000 title claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 title claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title claims description 10
- 239000010410 layer Substances 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 238000005401 electroluminescence Methods 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000012044 organic layer Substances 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 16
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 abstract description 10
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 238000000034 method Methods 0.000 abstract description 5
- 238000004528 spin coating Methods 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 3
- 239000002356 single layer Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 238000001771 vacuum deposition Methods 0.000 abstract 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 230000005540 biological transmission Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 230000008021 deposition Effects 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical group NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 2
- -1 3-aminomethyl phenyl Chemical group 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 206010009866 Cold sweat Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000005424 photoluminescence Methods 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000012916 structural analysis Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ZSYMVHGRKPBJCQ-UHFFFAOYSA-N 1,1'-biphenyl;9h-carbazole Chemical group C1=CC=CC=C1C1=CC=CC=C1.C1=CC=C2C3=CC=CC=C3NC2=C1 ZSYMVHGRKPBJCQ-UHFFFAOYSA-N 0.000 description 1
- QQLIGMASAVJVON-UHFFFAOYSA-N 1-naphthalen-1-ylethanone Chemical compound C1=CC=C2C(C(=O)C)=CC=CC2=C1 QQLIGMASAVJVON-UHFFFAOYSA-N 0.000 description 1
- VDULMXJUOWIPGE-UHFFFAOYSA-N 1-phenylisoquinoline quinoline Chemical compound N1=CC=CC2=CC=CC=C12.C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12 VDULMXJUOWIPGE-UHFFFAOYSA-N 0.000 description 1
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 1
- NRSBAUDUBWMTGL-UHFFFAOYSA-N 2-(1-benzothiophen-2-yl)pyridine Chemical compound S1C2=CC=CC=C2C=C1C1=CC=CC=N1 NRSBAUDUBWMTGL-UHFFFAOYSA-N 0.000 description 1
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920001088 polycarbazole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Abstract
The present invention relates to an iridium coordination compound on the basis of quinoline nitrogen heterocycles as ligands, and a preparation method and application thereof in organic electroluminescent devices as a red light material. In the method, a series of quinoline nitrogen heterocycles are selected as ligands and are coordinated with iridium (III) for forming iridium (III) coordination compounds; the iridium (III) coordination compounds are mixed in main body materials by a vacuum evaporation method or a solution spin coating method for structuring multilayer devices or single-layer devices for realizing high efficiency red light emission. Compared with other red light ligands, quinoline ligands have the characteristics of easy synthesis and purification; the corresponding coordination compound keeps short service life and high efficiency and provides possibility for structuring high efficiency electroluminescent devices.
Description
Technical field
The present invention relates to based on nitrogen heterocycles in quinoline is the complex of iridium of part and as the application of red light material in organic electroluminescence device.
Technical background
People such as C.W.Tang had reported 8-hydroxyquinoline aluminum (Alq first in 1987
3) electro optical phenomenon since, the research of Organic Light Emitting Diode has caused the extensive interest of academia and industrial community.According to the spin statistical theory, in most Organic Light Emitting Diodes, the singlet exciton of generation and the ratio of triplet excitons are 1: 3.The essence that triplet excitons is prohibited owing to long life-span and spin shows as non-radiative decay, thereby the internal quantum efficiency that has limited device can not surpass 25%.And transition metal complex is because the heavy atoms effect of atoms metal, caused very strong spin one track coupling, thereby increased effective singlet to the intersystem crossing between the triplet state, promptly utilize transition metal complex can make full use of all form of energy that comprise singlet and triplet state as electroluminescent material, increase substantially the efficient of device, can make the internal quantum efficiency of device reach 100% in theory.
Transition metal complex as electroluminescent material mainly contains Ir (III), Pt (II), Os (II), Re (I), Cu heavy metal complexes such as (I) at present. and wherein complex of iridium is widely used in the electroluminescent device owing to having short life-span and higher efficient, and has realized that red-green-blue is luminous.
The glow color of complex of iridium depends on the structure of part strongly, and therefore, we can select suitable part to regulate glow color.At present, the part that is used to obtain efficient ruddiness in the complex of iridium mainly contains 2-(2-benzothienyl) pyridine and 1-phenyl isoquinolin quinoline etc.The synthetic method complexity of these parts, and be not easy a large amount of synthetic.Therefore, need the synthetic and relatively easy part of purifying of design to be used for complexes of red light iridium efficiently.
Summary of the invention
The purpose of this invention is to provide a kind of is the complexes of red light iridium electroluminescent material of part based on nitrogen heterocycles in quinoline.
The present invention has designed and synthesized a series of nitrogen heterocycles in quinoline as part, with iridium (III) coordination, forms title complex; And the method by vacuum evaporation or solution spin coating is complex doped in material of main part with iridium (III), and structure multilayer device or single layer device are realized efficient red emission.Compare with other ruddiness part, the quinoline part has synthetic and the characteristics such as easy of purifying, and corresponding title complex kept short life-span and higher efficient, for the structure high efficiency electroluminous device provides possibility.
Synthetic iridium of the present invention (III) title complex is monokaryon hexa-coordinate structure, has following basic structure:
In the general structure
Representative is the bidentate ligand of ligating atom with carbon and nitrogen, has following structure:
Wherein, R
1Be selected from aryl, the C6-C30 condensed aromatic ring yl of alkoxyl group, the C6-C30 of alkyl, the C1-C20 of hydrogen, fluorine, trifluoromethyl, cyano group, C1-C30, the heteroaryl of C2-C30; Ar1 is selected from a kind of in the following aromatic structure unit:
R wherein
2, R
4, R
6Alkyl for C1-C30; R
5Be hexyl or octyl group; R
3Be the arbitrarily alkyl of the C1-C30 of the position of substitution or the alkoxyl group of C1-C20; R
7Be selected from the alkyl of hydrogen, C1-C30, the alkoxyl group of C1-C20, the aryl of C6-C30; R
8Be the alkyl of C1-C30 or the alkoxyl group of C1-C20; X is oxygen or sulphur atom.
The title complex that the present invention is above-mentioned, Ar1 preferentially are selected from a kind of in the following condensed ring aromatic structure unit:
R
3Be the arbitrarily alkyl of the C1-C30 of the position of substitution or the alkoxyl group of C1-C20
The title complex that the present invention is above-mentioned has following structure:
The title complex that the present invention is above-mentioned has following structure:
All quinoline parts are all by Friedl nder prepared in reaction.This reaction is with dense H
2SO
4Be catalyzer, HAc is a solvent with ice, back flow reaction 16-24 hour.Products obtained therefrom separates with recrystallization or post purifies.
All iridium (III) title complex all makes by two-step reaction.At first,
Part and iridous chloride reaction generate the intermediate of chloride bridge; Then, the chlorine bridge is replaced generation iridium (III) title complex by methyl ethyl diketone (acac).
According to the present invention, a kind of organic electroluminescence device has one or more layers organic thin layer that forms between first electrode and second electrode, and wherein one deck organic layer comprises one or more title complexs above-mentioned as the present invention at least
The luminescent layer of electroluminescent device can adopt the vacuum method preparation of evaporation altogether, technology is as follows: the while evaporation under vacuum condition with iridium (III) title complex and small molecules material of main part, by two independently the quartz crystal oscillator control separately vaporator rate, thereby control both content.Between anode ITO and luminescent layer, introduce hole transmission layer by vacuum vapour deposition simultaneously, between metallic cathode and luminescent layer, introduce one to two layer of organic molecule layer, the structure multilayer device with hole barrier or electric transmission function.Small molecules as material of main part comprises 4,4 '-N, N '-two carbazole biphenyl (CBP), 2-(4-phenylbenzene)-5-(4-tert-butyl-phenyl)-1,3,4-oxadiazole (PBD), 1,3,5-three (2-N-phenyl benzimidazolyl-) benzene (TPBI), 3-(4-phenylbenzene)-5-(4-tert-butyl-phenyl)-4-(4-ethylphenyl)-1,2,4-triazole (TAZ) etc.In luminescent layer, the weight ratio of iridium (III) title complex and material of main part is 1-9: 100.
The luminescent layer of electroluminescent device also can adopt the method preparation of solution spin coating, and technology is as follows: with iridium (III) title complex and the blend of polymer main body material, be dissolved in chloroform CHCl
3In, be spin-coated on through polythiofuran derivative (PEDOT) and modify or, be prepared into luminescent layer without the ito glass surface of its modification.Polymer as material of main part comprises: the derivative of polystyrene support, polyhenylene, Polyvinyl carbazole, polycarbazole, poly-fluorenes or poly-fluorenes.The weight ratio of iridium (III) title complex and polymer main body material is 1-9: 100.In addition, can also further mix small molecules carrier transmission material: 2-(4-phenylbenzene)-5-(4-tert-butyl-phenyl)-1 in the luminescent layer, 3,4-oxadiazole (PBD), 1,3,5-three (2-N-phenyl benzimidazolyl-) benzene (TPBI), 3-(4-phenylbenzene)-5-(4-tert-butyl-phenyl)-4-(4-ethylphenyl)-1,2,4-triazole (TAZ), N, N '-two (3-aminomethyl phenyl)-N, N '-phenylbenzene-1,1 '-phenylbenzene-4,4 '-diamines (TPD) or N, N '-two (1-naphthyl)-N, N '-phenylbenzene-1,1 '-phenylbenzene-4,4 '-diamines (NPB).Load onto in set of devices, direct evaporation metal electrode behind the intact luminescent layer of spin coating is made single layer device; Also the vacuum available vapour deposition method further introduces one to two-layer organic molecule layer with hole barrier or electric transmission function between metal electrode and luminescent layer, the structure multilayer device.
Description of drawings
In conjunction with the accompanying drawings, will clearerly understand the present invention by the detailed description of exemplary embodiment, wherein:
Fig. 1 provides compound (1-NAPQ)
2Ir (acac) and (TPAPQ)
2The UV, visible light of Ir (acac) in dichloromethane solution absorbs (UV-Vib) spectrum and photoluminescence (PL) fluorescence Spectra;
Fig. 2 provides the brightness-voltage curve of the organic EL device of embodiment 2 manufacturings;
Fig. 3 provides the luminous efficiency of the organic EL device that embodiment 2 makes and the power efficiency change curve with brightness;
Fig. 4 provides the EL spectrum of embodiment 1 and 2 organic EL devices of making
Embodiment
Describe the present invention in detail with reference to following examples, following examples are illustrative purposes and do not plan to limit the scope of the invention.
＜reaction formula 1 〉
Synthetic embodiment 1: title complex (1-NAPQ)
2Ir's (acac) is synthetic
(1) ligand 1-NAPQ's is synthetic
Adjacent aminobenzophenone of 1.97g (10mmol) and 1.70g (10mmol) 1-acetonaphthone are dissolved in the 15ml Glacial acetic acid, slowly drip the 0.1ml vitriol oil, stir reflux.React after 18 hours cool to room temperature.Reaction mixture is slowly poured in the mixing solutions of 40ml water and 15ml strong aqua composition.The precipitation of separating out is clamminess, and uses dichloromethane extraction, washing repeatedly, anhydrous Na
2SO
4Drying is filtered, and rotary evaporation falls solvent, and post separates purifies, and obtains 2.85g product (productive rate 86%).
(2) the chlorine bridge is dimeric synthetic
Get 1.46g (4.4mmol) ligand 1-NAPQ and 0.705g (2mmol) IrCl
33H
2O adds in the 50ml round-bottomed flask; add ethylene glycol monomethyl ether 30ml again, distilled water 10ml takes a breath 3 times repeatedly; stirring heating under argon shield; be warming up to 130～140 ℃, behind the back flow reaction 36h, filter; the precipitation that obtains is with ethanol and distilled water wash; drying, post separates purification, gets dimer 1.28g (productive rate 72%)
(3) title complex (1-NAPQ)
2Ir's (acac) is synthetic
Get dimer 0.89g (0.5mmol); methyl ethyl diketone (acac) 0.20g (2mmol), anhydrous sodium carbonate 0.53g (5mmol), ethylene glycol monoemethyl ether 30ml; add in the 50ml round-bottomed flask; take a breath repeatedly 3 times, stirring heating under argon shield is warming up to 130～140 ℃; behind the back flow reaction 24h; filter, the gained solid uses mixed solvent (sherwood oil/methylene dichloride=2/1) to carry out column chromatography for separation, obtains 500 milligrams of the finished product.(productive rate 53%)
(4) title complex (1-NAPQ)
2The structural analysis of Ir (acac)
Determined the structure of this compound by NMR and ultimate analysis.
1H?NMR(300MHz，CDCl
3)：δ1.54(s，6H)，4.60(s，1H)，6.88(d，J＝8.2Hz，2H)，7.04(d，J＝8.4Hz，2H)，7.29(t，J＝7.4Hz，2H)，7.37-7.40(m，4H)，7.50(t，J＝7.6Hz，2H)，7.56-7.75(m，12H)，7.85(d，J＝7.2Hz，2H)，8.38(d，J＝8.6Hz，2H)，8.62(s，2H)，8.72(d，J＝8.5Hz，2H).
Theoretical value (C
55H
39N
2O
2Ir): C, 69.38; H, 4.13; N, 2.94. measured value: C, 69.30; H, 4.38; N, 2.69.
＜reaction formula 2 〉
Synthetic embodiment 2: title complex (TPAPQ)
2Ir's (acac) is synthetic
Synthetic method and synthetic embodiment 1 are similar.
(1) part TPAPQ's is synthetic
Adjacent aminobenzophenone of 1.97g (10mmol) and 2.87g (10mmol) 4-diphenylamino methyl phenyl ketone are dissolved in the 15ml Glacial acetic acid, slowly drip the 0.1ml vitriol oil, stir reflux.React after 20 hours cool to room temperature.Reaction mixture is slowly poured in the mixing solutions of 40ml water and 15ml strong aqua composition.The precipitation of separating out is clamminess, and uses dichloromethane extraction, washing repeatedly, anhydrous Na
2SO
4Drying is filtered, and rotary evaporation falls solvent, and post separates purifies, and obtains 3.59g product (productive rate 80%).
(2) the chlorine bridge is dimeric synthetic
Get 1.97g (4.4mmol) ligand 1-NAPQ and 0.705g (2mmol) IrCl
33H
2O adds in the 50ml round-bottomed flask; add ethylene glycol monomethyl ether 30ml again, distilled water 10ml takes a breath 3 times repeatedly; stirring heating under argon shield; be warming up to 130～140 ℃, behind the back flow reaction 48h, filter; the precipitation that obtains is with ethanol and distilled water wash; drying, post separates purification, gets dimer 1.46g (productive rate 65%)
(3) title complex (TPAPQ)
2Ir's (acac) is synthetic
Get dimer 1.12g (0.5mmol); methyl ethyl diketone (acac) 0.20g (2.0mmol) anhydrous sodium carbonate 0.53g (5mmol); ethylene glycol monoemethyl ether 30ml adds in the 50ml round-bottomed flask, takes a breath repeatedly 3 times; stirring heating under argon shield; be warming up to 130～140 ℃, behind the back flow reaction 24h, filter; the gained solid column separates purifies, and obtains 530 milligrams of the finished product (productive rate 45%).
(4) title complex (TPAPQ)
2The structural analysis of Ir (acac)
Determined the structure of this compound by NMR and ultimate analysis.
1H?NMR(300MHz，CDCl
3)：δ1.62(s，6H)，4.77(s，1H)，6.25(d，J＝2.1Hz，2H)，6.55(dd，J＝8.5，2.0Hz，2H)，6.80-6.91(m，20H)，7.42-7.59(m，16H)，7.68(s，2H)，7.74(d，J＝8.1Hz，2H)，8.58(d，J＝8.6Hz，2H)
Theoretical value (C
71H
53N
4O
2Ir): C, 71.88; H, 4.50; N, 4.72. measured value: C, 71.10; H, 4.49; N, 4.52.
Embodiment 1:
For the embodiment that provides, use title complex (1-NAPQ)
2Ir (acac) is entrained in the CBP material of main part and makes organic EL device.At first, at the N of the surperficial evaporation 50nm that is coated with ito glass, N '-two (1-naphthyl)-N, N '-phenylbenzene-1,1 '-phenylbenzene-4,4 '-diamines (NPB) is as hole transmission layer.Then, deposition CBP forms the luminescent layer of 30nm on hole transmission layer, and 3% (1-NAPQ) wherein mixes
2Ir (acac).At last, deposition goes up hole blocking layer (BCP:10nm), electron transfer layer (Alq successively
3: 40nm), interfacial layer (LiF:1nm) and negative electrode (Al:100nm).
The El element of gained is at 100cd/m
2Brightness under, luminous efficiency is 2.2cd/A, external quantum efficiency is 3.0%, emission peak is at 642nm, peak width at half height is 35nm, chromaticity coordinates CIE value x=0.71, y=0.29.
Embodiment 2:
For this embodiment, use title complex (TPAPQ)
2Ir (acac) is entrained in the CBP material of main part and makes organic EL device.At first, at the N of the surperficial evaporation 50nm that is coated with ito glass, N '-two (1-naphthyl)-N, N '-phenylbenzene-1,1 '-phenylbenzene-4,4 '-diamines (NPB) is as hole transmission layer.Then, deposition CBP forms the luminescent layer of 30nm on hole transmission layer, and 7% (TPAPQ) wherein mixes
2Ir (acac).At last, deposition goes up hole blocking layer (BCP:10nm), electron transfer layer (Alq successively
3: 40nm), interfacial layer (LiF:1nm) and negative electrode (Al:100nm).
The El element of gained is at 100cd/m
2Brightness under, luminous efficiency is 12.2cd/A, external quantum efficiency is 9.0%, emission peak is at 616nm, peak width at half height is 48nm, chromaticity coordinates CIE value x=0.67, y=0.32.
Claims (5)
1. complexes of red light iridium that nitrogen heterocycles in quinoline is a part has following basic structure:
In the general structure
Representative is the bidentate ligand of ligating atom with carbon and nitrogen, has following structure:
Wherein, R
1Be selected from aryl, the C6-C30 condensed aromatic ring yl of alkoxyl group, the C6-C30 of alkyl, the C1-C20 of hydrogen, fluorine, trifluoromethyl, cyano group, C1-C30, the heteroaryl of C2-C30; Ar1 is selected from a kind of in the following aromatic structure unit:
R wherein
2, R
4, R
6Alkyl for C1-C30; R
5Be hexyl or octyl group; R
3Be the arbitrarily alkyl of the C1-C30 of the position of substitution or the alkoxyl group of C1-C20; R
7Be selected from the alkyl of hydrogen, C1-C30, the alkoxyl group of C1-C20, the aryl of C6-C30; R
8Be the alkyl of C1-C30 or the alkoxyl group of C1-C20; X is oxygen or sulphur atom.
2. an organic electroluminescence device has one or more layers organic thin layer that forms between first electrode and second electrode, and wherein one deck organic layer comprises one or more title complexs as claimed in claim 1 at least.
3. title complex as claimed in claim 1, Ar1 preferentially are selected from a kind of in the following condensed ring aromatic structure unit:
R
3Be the arbitrarily alkyl of the C1-C30 of the position of substitution or the alkoxyl group of C1-C20.
4. title complex as claimed in claim 1 has following structure:
5. title complex as claimed in claim 1 has following structure:
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