CN102718804A - GIr (green iridium) (III) composition as well as preparation method of GIr (III) composition and application of of GIr (III) composition to organic electroluminescence - Google Patents
GIr (green iridium) (III) composition as well as preparation method of GIr (III) composition and application of of GIr (III) composition to organic electroluminescence Download PDFInfo
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- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 18
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title claims description 8
- 150000001412 amines Chemical class 0.000 claims abstract description 28
- 239000003446 ligand Substances 0.000 claims abstract description 25
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 5
- 235000011164 potassium chloride Nutrition 0.000 claims description 5
- 239000001103 potassium chloride Substances 0.000 claims description 5
- -1 (2-naphthyl) phosphorus Chemical compound 0.000 claims description 4
- 238000005660 chlorination reaction Methods 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 230000006837 decompression Effects 0.000 claims description 3
- 239000005457 ice water Substances 0.000 claims description 3
- 150000002978 peroxides Chemical class 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000005051 trimethylchlorosilane Substances 0.000 claims description 3
- RSSDWSPWORHGIE-UHFFFAOYSA-N $l^{1}-phosphanylbenzene Chemical class [P]C1=CC=CC=C1 RSSDWSPWORHGIE-UHFFFAOYSA-N 0.000 claims description 2
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 abstract description 9
- KGZSSIFFYUBVOX-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]pyridine Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=N1 KGZSSIFFYUBVOX-UHFFFAOYSA-N 0.000 abstract 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 238000010189 synthetic method Methods 0.000 abstract 1
- 238000005481 NMR spectroscopy Methods 0.000 description 21
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 19
- 238000000921 elemental analysis Methods 0.000 description 18
- 239000000463 material Substances 0.000 description 16
- 239000010410 layer Substances 0.000 description 11
- 238000001228 spectrum Methods 0.000 description 9
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 7
- 238000001819 mass spectrum Methods 0.000 description 7
- 238000000862 absorption spectrum Methods 0.000 description 6
- 238000007740 vapor deposition Methods 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 238000002484 cyclic voltammetry Methods 0.000 description 4
- 238000006392 deoxygenation reaction Methods 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- IIYVNMXPYWIJBL-UHFFFAOYSA-N 4-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=NC=C1 IIYVNMXPYWIJBL-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 239000008358 core component Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention relates to an iridium (III) composition. A main ligand of the iridium (III) composition is 2-(4- trifluoromethyl phenyl) pyridine, an auxiliary ligand is di-(dibasic phenyl phosphinylidyne) amine or bi-(bi-2-naphthyl phosphinylidyne) amine, the iridium (III) composition has the following structural formula shown as the accompanying drawing, and an ITO (indium tin oxide)/TAPC (40nm)/GIr (green iridium)4 (x weight percent): mCP(20nm)/TPBi(40nm)/LiF(laser induce fluorescence) (1nm)/Al(100nm) electrofluorescence device structure is adopted. When the doping concentration of the GIr4 is 5 percent, the best device performance is reached, the power efficiency reaches as high as 113.23 lm/W, the current efficiency reaches as high as 115.39 cd/A, and in addition, the device reaches the maximum brightness being 49273 cd/m<2> at the driving voltage being 12V. The invention discloses a structure and a synthetic method of the composition as well as a structure and a manufacture method of an organic electroluminescence device.
Description
Technical field
The present invention relates to complex of iridium, also include organic electroluminescence devices.
Background technology
Organic electroluminescence device (Organic Light-emitting Diodes, be called for short OLEDs) is claimed Organic Light Emitting Diode again, is to apply voltage therein and the device that electric energy is converted into luminous energy.From the Tang of Kodak in 1987 [referring to Tang, C.W.; Vanslyke; S.A.Appl.Phys.Lett.1987; 51,913] delivered since the double-deck electroluminescent of small molecules organic film (EL) device of efficient high brightness of low voltage starting, the research of electroluminescent material and device has caused the very big interest of world technology circle and industry member.The OLEDs device is the flat panel display that has less energy-consumption, wide viewing angle, big area, can realize advantages such as soft screen; Be by generally believing that the next generation can replace indicating meters such as liquid crystal LCD, inorganic LED, can be used in mobile phone, the desirable image display of colour TV etc., demonstrating tempting prospect aspect solid-state illumination (solid-state lighting) and the FPD.
The structure of carrier transmission material, luminescent material, electrode materials and device that the distinct advantages of OLEDs device and device adopt has relation closely, and wherein luminescent material is the core component of OLEDs device.From Ma Yuguang in 1998 professor [referring to Y.G.Ma, H.Y.Zhang, J.C.Shen, C.M.Che, Synth.Met., 1998,94 (3), 245] and Forrest group [referring to Baldo, M.A.; O ' Brien, D.F.; You, Y.; Shoustikov, A.; Sibley, S.; Thompson, M.E.; Forrest; S.R.Nature1998,395,151] report electromechanical phosphorescent material owing to can gather in the crops singlet state and triplet exciton simultaneously; Make the internal quantum efficiency of OLEDs have to reach 100% potential maybe since, the research of heavy metal electromechanical phosphorescent material is increasingly extensive.Wherein, has good thermostability, short relatively lifetime of excited state because Ir (III) title complex is the MLCT luminescent ligand compound of a quasi-representative; High luminous efficiency, and glow color is prone to many-sided advantage such as adjusting and becomes the electroluminescent material hot research fields [referring to (a) A.B.Tamayo, B.D.Alleyne; P.L.Djurovich; Et.al.J.Am.Chem.Soc., 2003,7377; (b) S.Lamansky, P.L.Djurovich, D.Murphy, et alInorg.Chem., 2001,40,1704; (c) H.Rudmann, S.Shimada., M.F.Rubner, J.Am.Chem.Soc., 2002,124,4918; (d) J.P.Duan, P.P.Sun, C.H.Cheng, Adv.Mater., 2003,15,224; (e) Y.H.Song, S.J.Yeh, C.T.Chen, et al.Adv.Funct.Mater., 2004,14,1221; (f) C.L.Li, Y.J.Su, Y.T.Tao, et al.Adv.Funct.Mater., 2005,15,387; (g) Z.Q.Chen, Z.Q.Bian, C.H.Huang, Adv.Mater.2010,22,1534; (h) H.H.Chou, C.H.Cheng, Adv.Mater.2010,22,2468; (i) H.Z.Wu, T.S.Yang, Q.Zhao, et al.Dalton Trans.2011,40,1969; (j) H.J.Seo, M.Song, S.H.Jin, et al.Rsc Advances2011,1,755; (k) M.R.Zhu, T.L.Ye, X.He, et al.J.Mater.Chem.2011,21,9326; (l) L.X.Xiao, Z.J.Chen, B.Qu, et al.Adv.Mater.2011,23,926; (m) Y.C.Zhu, L.Zhou, H.Y.Li, et al.Adv.Mater.2011,23,4041.].This type title complex is owing to exist heavy atoms effect, and quantum yield can reach 100% in theory, has unique optical physics, spectrochemical property, is the good alternative materials of OLEDs luminescent layer, and very big researching value is arranged.
For these reasons with we before work [referring to (a) Y.C.Zhu, L.Zhou, H.Y.Li, et al Adv.Mater.2011,23,4041; (b) M.Y.Teng; S.Zhang, S.W.Jiang, et al.Appl.Phys.Lett.2012; 100; 073303.], the present invention has designed one type 9 novel Ir (III) title complex, and introducing 2-(4-trifluoromethyl) pyridine is that main part, two (phenylbenzene phosphinylidyne) sulfonamide derivatives are as assistant ligand.Because the methyl ethyl diketone assistant ligand that two (phenylbenzene phosphinylidyne) sulfonamide derivatives parts are commonly used relatively has electron transport ability preferably; In the device of preparation, widen the zone of electronics-hole-recombination in the luminescent layer, improved the luminosity of device and the stability of efficient.
Summary of the invention
The present invention provides 9, and to contain 2-(4-trifluoromethyl) pyridine be that main part, two (di-substituted-phenyl phosphinylidyne) amine or two (two-2-naphthyl phosphinylidyne) amine are the complex of iridium of assistant ligand and are organic electroluminescence device of luminescence center and preparation method thereof with it.
Technical scheme of the present invention is following:
A kind of iridium (III) title complex; They are GIr1, GIr2, GIr3, GIr4, GIr5, GIr6, GIr7, GIr8 or GIr9; It is characterized in that: their main part is 2-(4-trifluoromethyl) pyridine; Assistant ligand is two-(di-substituted-phenyl phosphinylidyne) amine or two-(two-2-naphthyl phosphinylidyne) amine, and they have following structural formula:
Wherein:
A kind of method for preparing the assistant ligand and iridium (III) title complex of above-mentioned title complex comprises the following steps:
Step 1. assistant ligand two-(di-substituted-phenyl phosphinylidyne) amine L1-L9's is synthetic:
Under the anhydrous and oxygen-free operation, disubstituted phenyl phosphorus of 8.0mmol chlorination or chlorination two (2-naphthyl) phosphorus reflux in dry toluene, slowly drip the 4.0mmol hmds; Drip Bi Jixu and under reflux state, reacted 6 hours, after reaction finishes, cooling; The byproduct of reaction trimethylchlorosilane is removed in decompression; Under ice-water bath, drip the ydrogen peroxide 50 that is dissolved in 30% in the THF (THF), reacted 2 hours, add the 100mL ether; Get white solid two-(di-substituted-phenyl phosphinylidyne) amine or two-(two-2-naphthyl phosphinylidyne) amine L1-L9, its structure is following:
Wherein:
Characterized and confirmed the structure of these parts with 1H NMR, mass spectrum, ultimate analysis (C, H, N); Detecting used instrument is Bruker DRX500 type NMR, Bruker Autoflex II TOF/TOF spectrometer mass spectrum workstation, Vario MICRO elemental analyser.Its reaction can be represented by following formula:
Step 2.Ir (III) title complex GIr-GIr9's is synthetic
Under the anhydrous and oxygen-free operation; Will two-{ two [2-(4-trifluoromethyl) pyridines] close iridochloride } and the sylvite of sylvite or two-(two-2-naphthyl phosphinylidyne) amine of two-(di-substituted-phenyl phosphinylidyne) amine of 2.5 times of amount of substances be dissolved in the ethylene glycol monoethyl ether; Reacted 12 hours down at 140 ℃; Filter, recrystallization, distillation is at last purified and is obtained corresponding title complex GIr-GIr9.Its reaction formula is following:
Complex of iridium of the present invention all is luminous extraordinary green luminescent material, and after the introducing of two-(di-substituted-phenyl phosphinylidyne) different amine or two-(two-2-naphthyl phosphinylidyne) amine assistant ligand, emission wavelength does not have big variation; Just luminous intensity has strong and weak other; Can be used for the luminescence center in the electroluminescent device, be electronic transmission performance and luminescent properties preferably luminescent layer [referring to the inventor's work: (a) Y.C.Zhu, L.Zhou; H.Y.Li; Et al.Adv.Mater.2011,23,4041; (b) M.Y.Teng, S.Zhang, S.W.Jiang, et al.Appl.Phys Lett.2012,100,073303.].
Use
1H NMR, mass spectrum, ultimate analysis (C, H, N), ultraviolet and emmission spectrum characterize and have confirmed the structure of these complex of iridium, and detecting used instrument is Bruker DRX 500 type NMRs, Bruker Autoflex II TOF/TOF spectrometer mass spectrum workstation, Vario MICRO elemental analyser, UV-3100 ultraviolet-visible spectrophotometer and Hitachi F-4600 luminoscope.
(3) title complex GIr4 is the device architecture of luminescence center, and the structure of the material of its structure and usefulness is following:
Adopt ITO/TAPC (40nm)/GIr4 (x wt%): mCP (20nm/TPBi (40nm)/LiF (1nm)/Al (100nm) electroluminescent device structure.Wherein, TAPC is as hole transmission layer, and mCP is the material of main part of phosphorescence twinkler, and TmPyPB is as electron transfer layer and hole blocking layer, and LiF is as electron injecting layer.All devices all present the green emission of title complex GIr4 under different doping contents and different current density, emission peak positions is at 521nm, and chromaticity coordinates is x=0.26, y=0.68.They all have low trigger voltage (3.2-3.3V), high power efficiency (58.93-113.23lm/W), high current efficiency (67.56-115.39cd/A).In doping content is 5% o'clock, has reached best device performance, and its power efficiency is up to 113.23lm/W, and current efficiency is up to 115.39cd/A, and device is issued to high-high brightness 49273cd/m2 at the driving voltage of 12V.Be the green device field of twinkler with Ir (III) title complex, such device performance is in the row of the best device performance of present report.The premium properties of device shows that these two kinds of title complexs have using value in the preparation of organic electroluminescence device.
Description of drawings
With title complex GIr4 is example:
Fig. 1: the crystal ellipsoid figure of title complex GIr4, ellipsoid probability are 30% (for clarity sake, Wasserstoffatoms omits);
Fig. 2: the uv absorption spectrum of title complex GIr4 in the toluene solution of deoxygenation;
Fig. 3: the emmission spectrum of title complex GIr4 in the toluene solution of deoxygenation;
Fig. 4: the life-span extinction curve of title complex GIr4 in the dichloromethane solution of deoxygenation;
Fig. 5: title complex GIr4 at CH
3CN/CH
2Cl
2(1:1) in the solution, sweep velocity is the cyclic voltammetry curve of 100mV/s;
Fig. 6: the TG-DTA curve of title complex GIr4;
The EL spectrum of Fig. 7: electroluminescent device ITO/TAPC (40nm)/GIr4 (5wt%): mCP (20nm)/TmPyPB (40nm)/LiF (1nm)/Al (100nm);
Power efficiency-current density curve of Fig. 8: electroluminescent device ITO/TAPC (40nm)/GIr4 (5wt%): mCP (20nm)/TmPyPB (40nm)/LiF (1nm)/Al (100nm).
Current efficiency-current density curve of Fig. 9: electroluminescent device ITO/TAPC (40nm)/GIr4 (5wt%): mCP (20nm)/TmPyPB (40nm)/LiF (1nm)/Al (100nm).
Luminous intensity-voltage-to-current density characteristic curve of Figure 10: electroluminescent device ITO/TAPC (40nm)/GIr4 (5wt%): mCP (20nm)/TmPyPB (40nm)/LiF (1nm)/Al (100nm);
Embodiment
Title complex of the present invention can synthesize according to following equation:
Wherein two-(phenylbenzene phosphinylidyne) sulfonamide derivatives and 4-trifluoromethyl pyridine ligand, two bridge title complexs all are [referring to (a) S.W.Magennis, S.Parsons, Z.Pikramenou, Chem.Eur.J., 2002,8,245761 according to the method for document preparation; (b) Y.M.You, S.Y.Park, J.Am.Chem.Soc., 2005,127,12438.], target title complex GIr-GIr9 is that the inventor prepares with improved compound method.Proton nmr spectra is measured on Bruker AM500 type NMR; Mass spectrum adopts the Autoflex II type mass spectrograph of Bruker company to measure MALDI-TOF-MS; The ultimate analysis of C, H, N records on Vario MICRO elemental analyser; Absorption spectrum and emmission spectrum record on Shimadzu3600 and Hitachi F-4600 spectrograph respectively; Phosphorescent lifetime is on Edinburgh FSL-920 spectrograph, to record, and thermogravimetric-DTA is carried out on STA449F3 (NETZSCH) thermogravimetric-differential thermal analyzer.Cyclic voltammetry experiment is on IM6ex (Zahner) electrochemical workstation, to carry out; With the platinum disk electrode is working electrode, and platinum wire electrode is a counter electrode, and the Ag/AgCl electrode is a reference electrode; At methylene dichloride: measure in acetonitrile=1:1 solution, wherein contain the n-Bu of 0.1M
4NClO
4As supporting electrolyte, with Fc
+/ Fc is interior mark, and sweep velocity is 100mV/s.OLEDs is lower than 1 * 10 at vacuum chamber pressure
-5Vapor deposition prepares in the vacuum plating unit of Pa, and the brightness of device and the sign of efficient adopt computer-controlled Keithley Source 2400/2000, PR650 current-voltage-nitometer, and electroluminescent spectrum records on Hitachi F-4600 spectrograph.
Embodiment one: assistant ligand two-(di-substituted-phenyl phosphinylidyne) amine L1-L9's is synthetic
Under the anhydrous and oxygen-free operation, the di-substituted-phenyl phosphorus chloride of 8.0mmol different substituents or two-(2-naphthyl) phosphorus chloride reflux in the dry toluene of 30mL, slowly drip the 4.0mmol hmds; Dripping Bi Jixu reacted 6 hours under reflux state; After reaction finishes, cooling, the byproduct of reaction trimethylchlorosilane is removed in decompression; Under ice-water bath, drip the ydrogen peroxide 50 that is dissolved in 30% among the THF; Reacted 2 hours, and added the 100mL ether, get white solid two-(di-substituted-phenyl phosphinylidyne) amine or two-(two-2-naphthyl phosphinylidyne) amine L1-L9.The part warp
1H NMR, mass spectrum, ultimate analysis verify that the result shows that structure is correct, and data are following:
Ligand L 1:
Productive rate: 62%.
1H?NMR(500MHz,CDCl
3,ppm)δ2.34(s,12H),7.50(d,8H),7.70(dd,8H),11.20(s,1H)。
MS(MALDI-TOF):m/z472.48[M]
+。
Results of elemental analyses: calculated value: C (%): 71.03H (%): 6.17N (%): 2.96
Measured value: C (%): 71.00H (%): 6.20N (%): 2.98.
Ligand L 2:
Productive rate: 68%.
1H?NMR(500MHz,CDCl
3,ppm)δ3.84(s,12H),6.99(dd,8H),7.68(d,8H),11.21(s,1H)。
MS(MALDI-TOF):m/z536.48[M]
+。
Results of elemental analyses: calculated value: C (%): 62.57H (%): 5.44N (%): 2.61
Measured value: C (%): 62.53H (%): 5.47N (%): 2.64.
Ligand L 3:
Productive rate: 72%.
1H?NMR(500MHz,CDCl
3,ppm)δ7.24(dd,8H),7.76(d,8H),11.19(s,1H)。
MS(MALDI-TOF):m/z488.34[M]
+。
Results of elemental analyses: calculated value: C (%): 58.91H (%): 3.50N (%): 2.86
Measured value: C (%): 58.87H (%): 3.52N (%): 2.88.
Ligand L 4:
Productive rate: 76%.
1H?NMR(500MHz,CDCl
3,ppm)δ7.70(dd,8H),7.50(d,8H),11.22(s,1H)。
MS(MALDI-TOF):m/z688.37[M]
+。
Results of elemental analyses: calculated value: C (%): 48.78H (%): 2.49N (%): 2.03
Measured value: C (%): 48.73H (%): 2.52N (%): 2.06.
Ligand L 5:
Productive rate: 73%.
1H?NMR(500MHz,CDCl
3,ppm)δ2.34(s,24H),6.91(dd,8H),7.35(d,4H),11.21(s,1H)。
MS(MALDI-TOF):m/z528.59[M]
+。
Results of elemental analyses: calculated value: C (%): 72.57H (%): 7.04N (%): 2.64
Measured value: C (%): 72.53H (%): 7.07N (%): 2.66.
Ligand L 6:
Productive rate: 71%.
1H?NMR(500MHz,CDCl
3,ppm)δ7.52(dd,8H),8.00(d,4H),11.20(s,1H)。
MS(MALDI-TOF):m/z960.36[M]
+。
Results of elemental analyses: calculated value: C (%): 39.98H (%): 1.36N (%): 1.46
Measured value: C (%): 39.95H (%): 1.38N (%): 1.49.
Ligand L 7:
Productive rate: 64%.
1H?NMR(500MHz,CDCl
3,ppm)δ11.22(s,1H)。
MS(MALDI-TOF):m/z776.19[M]
+。
Results of elemental analyses: calculated value: C (%): 37.09H (%): 0.13N (%): 1.80
Measured value: C (%): 37.04H (%): 0.16N (%): 1.82.
Ligand L 8:
Productive rate: 61%.
1H?NMR(500MHz,CDCl
3,ppm)δ11.23(s,1H)。
MS(MALDI-TOF):m/z976.21[M]
+。
Results of elemental analyses: calculated value: C (%): 34.41H (%): 0.10N (%): 1.43
Measured value: C (%): 34.37H (%): 0.11N (%): 1.45.
Ligand L 9:
Productive rate: 55%.
1H?NMR(500MHz,CDCl
3,ppm)δ7.32(t,4H),7.55(d,12H),8.09(d,12H),11.21(s,1H)。
MS(MALDI-TOF):m/z616.62[M]
+。
Results of elemental analyses: calculated value: C (%): 77.79H (%): 4.73N (%): 2.27
Measured value: C (%): 77.76H (%): 4.76N (%): 2.29
Embodiment two: Ir (III) title complex GIr-GIr9's is synthetic
Under the anhydrous and oxygen-free operation; The sylvite of inciting somebody to action two-(di-substituted-phenyl phosphinylidyne) amine or two-(two-2-naphthyl phosphinylidyne) amine of two-{ two [2-(4-trifluoromethyl) pyridines] close iridochloride } and 2.5 times of amount of substances is dissolved in the ethylene glycol monoethyl ether; Reacted 12 hours down at 140 ℃; Filter, recrystallization, distillation is at last purified and is obtained corresponding title complex GIr-GIr9.The part warp
1H NMR, mass spectrum, ultimate analysis verify that the result shows that structure is correct, and data are following:
Title complex GIr1:
Productive rate: 47%.
1H?NMR(500MHz,CDCl
3)δ8.87(d,2H),8.33(d,2H),7.99(dd,2H),7.74-7.62(m,10H),7.52(d,4H),7.24(d,8H)7.01(d,2H)。
MS(MALDI-TOF):m/z1110.06[M+1]
+。
Results of elemental analyses: calculated value: C (%): 56.31H (%): 3.82N (%): 3.79
Measured value: C (%): 56.27H (%): 3.84N (%): 3.83
Title complex GIr2:
Productive rate: 46%.
1H?NMR(500MHz,CDCl
3)δ8.88(d,2H),8.35(d,2H),8.01(dd,2H),7.76-7.64(m,10H),7.54(d,4H),7.04(d,10H),3.84(s,12H)。
MS(MALDI-TOF):m/z1173.06[M+1]
+。
Results of elemental analyses: calculated value: C (%): 53.24H (%): 3.61N (%): 3.58
Measured value: C (%): 53.19H (%): 3.65N (%): 3.62
Title complex GIr3:
Productive rate: 52%.
1H?NMR(500MHz,CDCl
3)δ8.85(d,2H),8.32(d,2H),7.97(dd,2H),7.80-7.66(m,10H),7.51(d,4H),7.24(d,8H),7.01(d,2H)。
MS(MALDI-TOF):m/z1125.93[M+1]
+。
Results of elemental analyses: calculated value: C (%): 51.25H (%): 2.69N (%): 3.74
Measured value: C (%): 51.20H (%): 3.71N (%): 3.78
Title complex GIr4:
Productive rate: 49%.
1H?NMR(500MHz,CDCl
3)δ8.86(d,2H),8.34(d,2H),7.98(dd,2H),7.73-7.59(m,18H),7.49(d,4H),7.01(d,2H)。
MS(MALDI-TOF):m/z1326.05[M+1]
+。
Results of elemental analyses: calculated value: C (%): 47.14H (%): 2.28N (%): 3.17
Measured value: C (%): 47.17H (%): 2.32N (%): 3.24
The crystallographic data of title complex GIr4:
R
1 a=∑||F
o|-|F
c||/∑F
o|.wR
2 b=[∑w(F
o 2-Fc
2)
2/∑w(Fo
2)]
1/2
The main bond distance of title complex GIr4
and bond angle (°).
Title complex GIr5:
Productive rate: 55%.
1H?NMR(500MHz,CDCl
3)δ8.83(d,2H),8.30(d,2H),7.93(dd,2H),7.69(d,2H),7.48(d,4H),7.33(d,4H),7.05-6.89(m,10H),2.31(s,24H)。
MS(MALDI-TOF):m/z1166.17[M+1]
+。
Results of elemental analyses: calculated value: C (%): 57.73H (%): 4.33N (%): 3.61
Measured value: C (%): 57.69H (%): 4.35N (%): 3.65
Title complex GIr6:
Productive rate: 41%.
1H?NMR(500MHz,CDCl
3)δ8.76(d,2H),8.28(d,2H),8.01(d,4H),7.91(d,2H),7.69(d,2H),7.55-7.46(m,12H),6.98(d,2H)。
MS(MALDI-TOF):m/z1597.95[M+1]
+。
Results of elemental analyses: calculated value: C (%): 42.12H (%): 1.64N (%): 2.63
Measured value: C (%): 42.08H (%): 1.66N (%): 2.67
Title complex GIr7:
Productive rate: 34%.
1H?NMR(500MHz,CDCl
3)δ8.82(d,2H),8.34(d,2H),7.98(d,2H),7.73(d,2H),7.52(m,4H),7.02(d,2H)。
MS(MALDI-TOF):m/z1413.77[M+1]
+。
Results of elemental analyses: calculated value: C (%): 40.81H (%): 1.00N (%): 2.97
Measured value: C (%): 42.78H (%): 1.02N (%): 3.01
Title complex GIr8:
Productive rate: 32%.
1H?NMR(500MHz,CDCl
3)δ8.83(d,2H),8.35(d,2H),7.99(d,2H),7.75(d,2H),7.53(m,4H),7.03(d,2H)。
MS(MALDI-TOF):m/z1613.80[M+1]
+。
Results of elemental analyses: calculated value: C (%): 38.73H (%): 0.87N (%): 2.61
Measured value: C (%): 38.67H (%): 0.89N (%): 2.63
Title complex GIr9:
Productive rate: 44%.
1H?NMR(500MHz,CDCl
3)δ8.76(d,2H),8.28(d,2H),8.15-7.94(m,14H),7.73(d,2H),7.64-7.46(m,22H),7.02(d,2H)。
MS(MALDI-TOF):m/z1254.23[M+1]
+。
Results of elemental analyses: calculated value: C (%): 61.34H (%): 3.38N (%): 3.35
Measured value: C (%): 61.31H (%): 3.40N (%): 3.38
Embodiment three: the absorption spectrum of title complex GIr4 of the present invention, emmission spectrum and other signs
Complex of iridium of the present invention all is luminous extraordinary green luminescent material; After the introducing of two-(di-substituted-phenyl phosphinylidyne) different amine or two-(two-2-naphthyl phosphinylidyne) amine assistant ligand; Absorption and emission wavelength do not have big variation; Just luminous intensity has power other, and this also is the characteristic that contains the assistant ligand complex of iridium, and glow color mainly contains main part decision.Therefore we are that example has been listed its crystalline structure, absorption spectrum and emmission spectrum, life-span and chemical property and thermostability with title complex GIr4 just.Crystalline structure is on Siemens (Bruker) SMART CCD diffractometer, to record.Title complex GIr4 is dissolved in the toluene (10
-4M), deoxygenation, measure its absorption spectrum and emmission spectrum respectively at Shimadzu3600 and Hitachi F-4600 spectrograph, on Edinburgh FSL-920 spectrograph, record phosphorescent lifetime.Cyclic voltammetry experiment is on IM6ex (Zahner) electrochemical workstation, to carry out, and thermogravimetric-DTA is that pressed powder carries out on STA449F3 (NETZSCH) thermogravimetric-differential thermal analyzer.
At ambient temperature, the peak position of absorption spectrum and emmission spectrum is respectively:
λ
Abs, max, nm282,346,410,466 (seeing accompanying drawing 2);
λ
Em, max, nm517,549 (seeing accompanying drawing 3);
Be the spectral quality of two title complexs of objective evaluation, with [the Ru (bpy) of air saturation
3]
2+2Cl
-Acetonitrile solution be reference material, utilize title complex uv-absorbing and fluorescence emission spectrum data computation the fluorescence quantum efficiency of title complex GIr4 be 9.0%.
Title complex has relatively shorter phosphorescent lifetime: τ, μ s0.090 (seeing accompanying drawing 4);
Title complex GIr4 at CH
3CN/CH
2Cl
2(1:1) in the solution, sweep velocity is that the cyclic voltammetry curve of 100mV/s is seen accompanying drawing 5;
Title complex has reasonable thermostability, thermolysis initial temperature (mass loss corresponding to 5%):
Td, ° 362 (seeing accompanying drawing 6).
Embodiment four: be the preparation of the organic electroluminescent device OLED s of luminescence center with title complex GIr4
Device apparatus for preparation: multi-source OMBD system of Shenyang high-vacuum technology institute; Testing tool: Keithley Source2400/2000, PR650 current-voltage-nitometer, Hitachi F-4600 spectrograph.
The structure of device is: ITO/TAPC (40nm)/GIr4 (5wt%): mCP (20nm)/TmPyPB (40nm)/LiF (1nm)/Al (100nm)
The power efficiency of device (cd/A) is obtained by the I-V and the L-V characteristic of device:
η
p=L/I(1)
The ampere efficiency of device can be obtained by computes:
η
cπ×S×L/(I×V)(2)
Wherein, L is a luminous intensity, and I is a current density, and S is a light-emitting area, and V is for loading the voltage at electroluminescent device two ends.
Ito glass with 15 Ω/sq is a substrate; Clean up with glass cleaner earlier, use deionized water again, acetone each ultrasonic three times; Through the low oxygen plasma bombardment after 20 minutes; Carry out the organic layer vapor deposition, the hole mobile material TAPC of 40nm at first is deposited in the ito glass substrate, and guest materials and material of main part form the luminescent layer of 20nm through the form that is total to vapor deposition then; Next be electric transmission and the hole blocking layer TmPyPB of 40nm, the negative electrode aluminium of the cathode buffer layer/electron injecting layer of the LiF of 1nm and 100nm.Adopting area in the time of the negative electrode vapor deposition is 0.1cm
2Template stop.All organic materialss have all carried out the distillation of vacuum low-pressure gradient and have purified before vapor deposition.When the material vapor deposition, vacuum chamber pressure is lower than 1 * 10
-5Pa.The sign of device adopts computer-controlled Keithley Source 2400/2000, PR650 current-voltage-nitometer.Electroluminescent spectrum records on Hitachi F-4600 XRF.All measurements all record under atmosphere at room temperature, and the salient features of device is following:
The EL spectrum of electroluminescent device:
λ
EL, max, nm521 (seeing accompanying drawing 7);
The power efficiency of electroluminescent device-current density curve:
Maximum power efficiency η
P.max: 113.23lm/W (seeing accompanying drawing 8);
The current efficiency of electroluminescent device-current density curve.
The maximum current efficiency eta
C.max: 115.39cd/A (seeing accompanying drawing 9);
The luminous intensity of electroluminescent device G2 and BG2-voltage-to-current density characteristic curve: maximum luminousing brightness L
Max, cd/m
2: 49273cd/m
2(12V) (see accompanying drawing 10).
Claims (3)
1. an iridium (III) title complex; It is characterized in that: they are GIr1, GIr2, GIr3, GIr4, GIr5, GIr6, GIr7, GIr8 or GIr9; Their main part is 2-(4-trifluoromethyl) pyridine; Assistant ligand is two-(di-substituted-phenyl phosphinylidyne) amine or two-(two-2-naphthyl phosphinylidyne) amine, and they have following structural formula:
Wherein:
2. a method for preparing the described iridium of claim 1 (III) title complex is characterized in that comprising the following steps:
Step 1. assistant ligand two-(di-substituted-phenyl phosphinylidyne) amine or two-(two-2-naphthyl phosphinylidyne) amine L1-L9's is synthetic:
Under the anhydrous and oxygen-free operation, disubstituted phenyl phosphorus of 8.0mmol chlorination or chlorination two (2-naphthyl) phosphorus reflux in dry toluene, slowly drip the 4.0mmol hmds; Drip Bi Jixu and under reflux state, reacted 6 hours, after reaction finishes, cooling; The byproduct of reaction trimethylchlorosilane is removed in decompression; Under ice-water bath, drip the ydrogen peroxide 50 that is dissolved in 30% in the THF (THF), reacted 2 hours, add the 100mL ether; Get white solid two-(di-substituted-phenyl phosphinylidyne) amine or two-(two-2-naphthyl phosphinylidyne) amine L1-L9, its structure is following:
Wherein:
Step 2.Ir (III) title complex GIr-GIr9's is synthetic
Under the anhydrous and oxygen-free operation; Will two-{ two [2-(4-trifluoromethyl) pyridines] close iridochloride } and the sylvite of sylvite or two-(two-2-naphthyl phosphinylidyne) amine of two-(di-substituted-phenyl phosphinylidyne) amine of 2.5 times of amount of substances be dissolved in the ethylene glycol monoethyl ether; Reacted 12 hours down at 140 ℃; Filter, recrystallization, distillation is at last purified and is obtained corresponding title complex GIr-GIr9.
3. the application of the described iridium of claim 1 (III) title complex in the preparation organic electroluminescence device.
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