CN1421470A - Conjugated polymer containing oxdiazole and its application - Google Patents
Conjugated polymer containing oxdiazole and its application Download PDFInfo
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- CN1421470A CN1421470A CN 01139774 CN01139774A CN1421470A CN 1421470 A CN1421470 A CN 1421470A CN 01139774 CN01139774 CN 01139774 CN 01139774 A CN01139774 A CN 01139774A CN 1421470 A CN1421470 A CN 1421470A
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Abstract
The present invention discloses one kind of conjugated polymer containing oxidazole and with excellent electron injection and transmission capacity and its application as blue electroluminescence material in organic planar display device. The polymer has good dissolvability, heat stability, electronic transmission, color purity, etc.
Description
Technical field:
The present invention relates to a class contain uh diazole conjugated highpolymer and as the application of blue electroluminescent material in organic flat panel display device.
Background technology:
From Kodak (Tang, C.W. in 1987; Vanslyke, S.A.Appl.Phys.Lett.1987,51,913) and nineteen ninety univ cambridge uk (Burroughes, J.H.; Jones, C.A.; Friend, R.H.Nature 1990,335,137) released since efficient organic and the polymer electroluminescent device (LED) respectively, caused international competition one organic polymer panchromatic plane display material and the device in the worldwide in Materials science and areas of information technology.Advantages such as its luminous, high brightness, high-level efficiency, low dc voltage driving, low cost, the dependence of no visual angle, fast-response speed, thin, light, flexible good, big area and panchromatic demonstration have represented brilliant prospect for modern technique of display.This field is attracting the scientist of the different subjects of many countries and the concern and the input of increasing research institution and company.At present, many antetype devices have been succeeded in developing even have been entered the practicability stage.Before 2005, the market of organic polymer photodiode is in advance in respect of 3,500,000,000 dollars.The colored demonstration is the important goal that organic LED is pursued, and the red-green-blue device is all extremely important for realizing that colour shows.At present, ethereal blue light and red light material and device be seldom efficiently.In addition, high efficiency electroluminescent device injects by effective electric charge and the equilibrated charge transfer realizes.But injection of the hole of most organic polymer luminescent materials and transmittability are better than the injection and the transmission of electronics.Therefore, exploitation has that stable doping characteristic and outstanding electronics inject and the conjugated polymers of transmittability is particularly important.
Poly-fluorenes shows interesting and unique chemical and physical properties owing to its main chain contains the coplanar biphenyl of rigidity unit, can connect substituting group in 9 positions far away, can improve its processibility and solvability and do not increase sterically hindered on the skeleton like this, do not change effective conjugation degree yet, can control simultaneously interchain and interact, reduce the formation of excimer.In recent years, poly-fluorenes and derivative thereof are owing to their good stability and high fluorescence quantum yield become the most noticeable blue electroluminescent material (Yang, Y.; Pei, Q.J.Am.Chem.Soc.1996,118,7416).But the πDian Zi of the coplanar fluorenes interannular of rigidity interacts strong, and poly-fluorenes is assembled easily or easily formed excimer, causes phenomenons such as photoluminescent band is widened, red shift, concentration quenching to take place, and reduces the processing property of blue-light device greatly.
2-(4-xenyl)-5-(4-t-butyl-phenyl)-1,3,4-uh diazole (PBD) be widely used electronics injection and transport material or hole blocking material (Adachi, C.; Tsutsui, T.; Saito, S.Appl.Phys.Lett.1989,55,1489).Some contain uh diazole polymkeric substance oneself be used as electron transport material and luminescent material (1:Strukelj, M.; Papadimitrakopoulos, F.; Miller, T.M.; Rothberg, L.J.Science 1995,267,1969.2:Yu, W.-L.; Meng, H.; Pei, J.; Huang, W.J.Am.Chem.Soc.1998,120,11808).Generally speaking, the preparation of poly-uh diazole is to adopt the polyhydrazide precursor route.This synthesis path has two weakness: polyhydrazide is poorly soluble in common organic solvents, be difficult to purify, and impurity will be brought the ultimate aim product into like this, and the impurity of material has fatal influence to the processing property of device; Because polyhydrazide and final product are at dehydrated solvent such as POCl
3In poorly soluble, the cyclodehydration of polyhydrazide reaction is carried out not exclusively.
At present, the electron transport material of poly-fluorenes class lacks, do not have document and patent report fluorenes and uh the multipolymer of diazole and the application in organic electroluminescent thereof.
Summary of the invention:
The object of the present invention is to provide a class contain uh diazole have that stable doping characteristic and outstanding electronics inject and the conjugated highpolymer of transmittability and as the application of blue electroluminescent material at organic flat panel display device.
The present invention uh the outstanding electronic transmission performance of diazole and the efficient blue emission performance of poly-fluorenes be combined in the same polymkeric substance, with Suzuki condensation path of preparing a series of brand-new n-type fluorenes and uh the diazole multipolymer.Characterized the chemical structure of polymkeric substance with ultimate analysis, infrared spectra, nucleus magnetic resonance, with gel permeation chromatography their molecular weight, tested the thermostability of polymkeric substance with thermogravimetric analysis and differential thermal analysis, characterize their electrochemical properties with cyclic voltammetric, studied the photophysical property of these polymkeric substance with ultra-violet absorption spectrum and fluorescence spectrum.Experimental result shows that these multipolymers are electron transport material and blue electroluminescent materials of high comprehensive performance.
Of the present invention contain uh the conjugated highpolymer of diazole, its general formula is as follows:
M=1,2 M
w=20000-100000R
1And R
2Be normal-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl or positive certain herbaceous plants with big flowers base; Be preferably n-hexyl, n-octyl or 2-ethylhexyl; Most preferably be the 2-ethylhexyl.
Major advantage of the present invention is:
With Suzuki condensation path of preparing uh diazole and fluorene copolymer.
2. the synthetic polymer dissolution is good, and is solvable in organic solvents such as chloroform and tetrahydrofuran (THF).
3. Heat stability is good, initial heat decomposition temperature surpasses 394 ℃, and second-order transition temperature is above 137 ℃.
4. electron-transporting is good, and minimum not occupied orbital (LUMO) energy level is lower, is lower than-2.81eV.
5. all polymkeric substance are blue electroluminescent material, and emission wavelength is between 410-430nm; Emission band is narrower, peak width at half height (FWHM) between 70-85nm, high color purity.
Description of drawings: Fig. 1 is that polymer P-1 synthetic route Fig. 2 is that polymer P-1 and P-2 film uv absorption spectra 5 are polymer P-1 and P-2 film photoluminescence spectra for polymer P-2 synthetic route Fig. 3 for polymer P-1 cyclic voltammetry curve Fig. 4
Embodiment:
Synthetic route as depicted in figs. 1 and 2.(1) 9,9-two (2-ethylhexyl) fluorenes (being called for short compound 2)
Add 30mmol (4.98g) fluorenes (compound 1) in the 250mL there-necked flask, vacuumize applying argon gas 30min, inject the 95mL ether, be cooled to-78 ℃, drip 30mmol (18.75mL) 1.6M n-Butyl Lithium hexane solution with liquid nitrogen-acetone.Add 30mmol (5.79g) 2-ethylhexyl bromo-5mL Et behind the 2h
2O, reaction mixture stirs 4h at-78-20 ℃.Add the washing of 100mL deionization, use the 50mL extracted with diethyl ether, the anhydrous MgSO of oil reservoir
4Drying is taken out and is desolvated, and lyophilize gets faint yellow oily thing (10.76g, 92%) .Anal.Calcd for C
29H
42: C, 89.16; H, 10.84.Found:C, 88.67; H, 10.98%.m/z (EI) 390 (M
+).
1H NMR (300 MHz, CDCl
3): δ 7.64 (d, 2H), 7.33 (d, 2H), 7.23 (dd, 4H), 1.96 (br, 4H), 1.26 (s, 2H), 0.88-0.63 (m, 22H), 0.47 (t, 6H). (2) 2,7-two bromo-9,9-two (2-ethylhexyl) fluorenes (being called for short compound 3)
Add 64mmol (25g) compound 2 and 64mg iodine in the 500mL Erlenmeyer flask, add 160mL CH again
2Cl
2,, under lucifuge, drip 128mmol (21g) bromo-50mLCH with the ice bath cooling
2Cl
2About 0.5h then at room temperature stirs 24h.Add the 60mL20%KOH aqueous solution in reaction mixture, redness is taken off.Organic layer separates, washing, anhydrous MgSO
4Drying is taken out and is desolvated, and lyophilize gets orange (31g, 90%).Anal.Calcd forC
29H
40Br
2: C, 63.51; H, 7.35.Found:C, 63.22; H, 7.47%.m/z (EI) 548 (M
+).
1H NMR (300MHz, CDCl
3): δ 7.71 (d, 2H), 7.48 (d, 2H), 7.28 (d, 2H), 1.96 (br, 4H), 1.26 (s, 2H), 0.88-0.60 (m, 22H), 0.51 (t, 6H). (3) 9,9-two (2-ethylhexyl) fluorenes-2,7-hypoboric acid (being called for short compound 4)
Add 10mmol (5.5g) compound 3,25mmol (0.6g) magnesium chips, 0.06g iodine in the 100mL there-necked flask, inflated with nitrogen 30min injects 20mL THF, backflow 24h.Be chilled to-78 ℃ with liquid nitrogen-acetone, drip 25mmol (2.8mL) B (OCH
3)
3The about 45min of-10mL THF adds 40mL THF dilution again, at room temperature stirs 72h.Reaction mixture is poured into the dense H of 20mL
2SO
4In-200mL the frozen water, stir 2h, use extracted with diethyl ether, water washing, anhydrous MgSO
4Dry.Take out and desolvate, use acetone solution, splash into again among the dense HCl of 100mL, get white precipitate, filter, washing, 40 ℃ of vacuum-dryings get white solid (3.9g, 81%): 219 ℃ of MP.Anal.Calcd for C
29H
44O
4B
2: C, 72.83; H, 9.27.Found:C, 72.66; H, 9.17%.
1H NMR (300 MHz, DMSO-d
6): δ 8.26 (s, 4H), 7.92 (m, 2H), 7.80 (m, 2H), 7.70 (m, 2H), 1.95 (br, 4H), 1.20 (s, 2H), 0.79-0.58 (m, 22H), 0.42 (t, 6H) .FT-IR (KBr): v 3447,2958, and 2926,2857,1728,1608,1464,1421,1351,1324,1123,1075,742cm
-1. (4) 9,9-two (2-ethylhexyl) fluorenes-2,7-two (trimethylene boric acid ester) (being called for short compound 5)
Add 10mmol (4.8g) compound 4,21mmol (1.5mL) 1 in the 100mL there-necked flask, ammediol, 60mL toluene, logical nitrogen 30min, backflow 4h.Cooling is taken out and is desolvated, and uses ether dissolution, uses anhydrous CaCl again
2Drying is taken out and is desolvated, and lyophilize gets faint yellow viscous liquid (5.2g, 93%).Anal.Calcd for C
35H
52O
4B
2: C, 75.28; H, 9.39.Found:C, 75.66; H, 9.58%.
1H NMR (300 MHz, CDCl
3): δ 7.78 (d, 2H), 7.71 (d, 2H), 7.68 (d, 2H), 4.19 (t, 8H), 2.07 (t, 4H), 1.98 (d, 4H), 1.27 (s, 2H), 0.88-0.68 (m, 22H), 0.47 (t, 6H). (5) are to bromobenzene formyl hydrazine (being called for short compound 7)
Add 25mmol (5.7g) parabromobenzoic acid ethyl ester (compound 6), 75mmol (4.7mL) hydrazine hydrate, 25mL methyl alcohol in the 50mL there-necked flask, inflated with nitrogen, backflow 16h, freezing, get white needle-like crystals (5.1g, 95%): MP 166-167 ℃.Anal.Calcd forC
7H
7N
2OBr:C, 39.10; H, 3.28.Found:C, 39.23; H, 3.27%.
1HNMR (300 MHz, DMSO-d
6): δ 9.88 (s, 1H), 7.79 (d, 2H), 7.68 (d, 2H), 4.54 (s, 2H). the inferior hydrazine of (6) two (to the bromobenzene formyls) (being called for short compound 8)
Add 10mmol (2.15g) compound 7,10mmol (2.19g) parabromobenzoyl chloride, 50mL pyridine in the 50mL there-necked flask, inflated with nitrogen, backflow 6h, cooling adds 200mL ethanol, and is freezing, gets white plates crystal (3.2g, 80%): MP 319-320 ℃.Anal.Caicdfor C
14H
10N
2O
2Br
2: C, 42.24; H, 2.53.Found:C, 42.01; H, 2.57%.
1H NMR (300 MHz, DMSO-d
6): δ 10.63 (s, 2H), 7.85 (d, 4H), 7.77 (d, 4H). two pairs of bromophenyls-1,3 of (7) 2,5-, 4-uh diazole (be called for short compound 9)
Add 10mmol (4.0g) compound 8,10mL SOCl in the 50mL there-necked flask
2, inflated with nitrogen, backflow 5h steams solvent, cooling adds 50mL water, filter, through distillation purify white crystal (2.7g, 71%): 258 ℃ of MP.Anal.Caicd for C
14H
8N
2OBr
2: C, 44.25; H, 2.12.Found:C, 44.08; H, 2.17%.
1H NMR (300 MHz, DMSO-d
6): δ 8.00 (d, 4H), 7.68 (d, 4H). (8) poly-[2,7-9,9-two (2-ethylhexyl) fluorenes-alt-2, two pairs of penylenes-1,3 of 5-, 4-uh diazole] (being called for short polymer P-1)
Add 0.5mmol (190mg) compound 9 and 0.5mmol (280mg) compound 5 in the 50mL there-necked flask, inflated with nitrogen 30min adds 0.01mmol (11.5mg) Pd (PPh
3)
4, inject 5mL toluene, stir, be warming up to 120 ℃, 5mL 2M K reinjects
2CO
3, reaction mixture refluxed in nitrogen atmosphere 72 hours.Be chilled to room temperature, add CHCl
3Dilution, washing, the anhydrous MgSO of oil reservoir
4Drying is evacuated to 2mL, splashes in the 100mL methyl alcohol to precipitate.The solid of gained is dissolved in CHCl again
3, micro-filtration splashes in the 100mL methyl alcohol and precipitates, and gets pale yellow powder (228mg, 75%) through the methyl alcohol extracting.Anal.Calcd for (C
43H
48N
2O)
n: C, 84.83; H, 7.95.Found:C, 85.44; H, 8.17%.
1H NMR (300 MHz, CDCl
3): δ 8.21 (d, 4H), 7.78 (m, 6H), 7.63 (d, 4H), 2.08 (d, 4H), 1.19 (s, 2H), 0.81-0.46 (m, 28H) .FT-IR (KBr): 2961,2926,2872,2857,1613,1500,1465,1408,1378,1262,1098,1018,852,817,804,752cm
-1. solvability is good in organic solvents such as chloroform and tetrahydrofuran (THF).Weight-average molecular weight M
w20000, molecular weight distribution 2.3.400 ℃ of initial heat decomposition temperatures, 137 ℃ of second-order transition temperatures.(9) to dibenzoyl hydrazine (being called for short compound 11)
9.7g (50mmol), be heated to 60 ℃ of backflows and spend the night adding 50ml methyl alcohol and 14.53ml (300mmol) hydrazine hydrate in the dibenzoic acid methyl esters (compound 10), the solution layering, filter white solid (8.7g, 90%).MP：197℃。Anal.Calcd?for?C
8H
10N
4O
2：C，49.48；H，5.19；N，28.85.Found：C，49.13；H，5.26；N，29.07％。m/z(EI)：194(M
+)。(10) 1,4-2 (5-is to bromophenyl-1,3,4-uh diazole) benzene (being called for short compound 12)
Add 10mmol (1.94g) compound 11,10mmol (2.19g) parabromobenzoyl chloride, 50mL pyridine in the 50mL there-necked flask, inflated with nitrogen, backflow 6h.Add 10mL SOCl again
2, backflow 5h steams solvent, cooling adds 50mL water, filter, through distillation purify white crystal (3.35g, 64%).Mp：＞300℃.Anal.Calcd?for?C
22H
12Br
2N
4O
2：C，50.41；H，2.31；N，10.69.Found：C，50.13；H，2.36；N，10.77％.m/z(EI)：524(M
+)。
1H NMR (300MHz, DMSO-d
6): δ 8.04 (m, 4H), 7.85 (m, 4H), 7.75 (m, 4H). (11) poly-[2,7-9,9-two (2-ethylhexyl) fluorenes-alt-1,4-two (2-is to penylene-1,3,4-uh diazole) benzene] (being called for short polymer P-2)
Add 0.5mmol (262mg) compound 12 and 0.5mmol (280mg) compound 5 in the 50mL there-necked flask, inflated with nitrogen 30min adds 0.0lmmol (11.5mg) Pd (PPh
3)
4, inject 5mL toluene, stir, be warming up to 120 ℃, 5mL 2M K reinjects
2CO
3, reaction mixture refluxed in nitrogen atmosphere 72 hours.Be chilled to room temperature, add CHCl
3Dilution, washing, the anhydrous MgS0 of oil reservoir
4Drying is evacuated to 2mL, splashes in the 100mL methyl alcohol to precipitate.The solid of gained is dissolved in CHCl again
3, micro-filtration splashes in the 100mL methyl alcohol and precipitates, and gets pale yellow powder (357mg, 95%) through the methyl alcohol extracting.Anal.Calcd for (C
51H
52N
4O
2)
n: C, 81.35; H, 6.96.Found:C, 81.94; H, 7.13%.FT-IR (KBr): 2961,2913,2854,1601,1509,1462,1267,1091,805,464cm
-1. dissolve in organic solvents such as chloroform and tetrahydrofuran (THF).394 ℃ of initial heat decomposition temperatures, 194 ℃ of second-order transition temperatures.(12) electrochemical properties
Electrochemistry cyclic voltammetric (CV) experiment is at computer-controlled EG﹠amp; Finish on GPotentiostat/Galvanostat Model 283 voltammetric analyzers, adopt three-electrode system, polymkeric substance is coated on the platinum electrode as working electrode Ag/Ag
+Be reference electrode, platinum filament is a counter electrode, and anhydrous acetonitrile is made solvent, (C
4H
9)
4NPF
6Be supporting electrolyte.The CV curve of polymer P-1 is seen Fig. 3.Its oxidation and reduction peak are will definitely be contrary.According to literature method (Pommerehne, J.; Vestweber, H.; Guss, W.; Mahrt, R.F.; Bassler, H.; Porsch, M.; Daub, J.Adv.Mater.1995,7,551), make benchmark with ferrocene (FOC) and can calculate its lumo energy.The lumo energy of P-1 and P-2 be respectively-2.81 and-3.07eV, (2.4eV) also more much lower, so they are good electron transport materials than the lumo energy of famous electron transport material PBD.(13) luminosity
Fig. 4 has provided solid film uv-absorbing (UV) spectrum of polymer P-1 and P-2, and their maximum absorption band is respectively 369 and 352nm, by absorption spectrum calculate band gap be respectively 3.02 and 3.09eV.Big band gap is the precondition of blue emitting material.
The film of two kinds of polymkeric substance all sends strong blue light under ultra violet lamp.Fig. 5 has provided solid film photoluminescence (PL) spectrum of polymer P-1 and P-2, and their maximum emission peak is respectively 414 and 422nm, and peak width at half height is respectively 76 and 82nm, and is very narrow, illustrates that the purity of color of blue light is fine.Therefore they are up-and-coming blue light materials.
Claims (5)
1. contain uh the conjugated highpolymer of diazole, its general formula is as follows:
M=1.2 M
w=20000-100000R
1And R
2Be normal-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl or positive certain herbaceous plants with big flowers base.
According to containing of claim 1 uh the conjugated highpolymer of diazole, it is characterized in that; Described R
1And R
2Be n-hexyl, n-octyl or 2-ethylhexyl.
According to containing of claim 1 uh the conjugated highpolymer of diazole, it is characterized in that; Described R
1And R
2Be the 2-ethylhexyl.
Claim 1 contain uh the conjugated highpolymer of diazole as the application of blue electroluminescent material.
According to containing of claim 4 uh the conjugated highpolymer of diazole as the application of blue electroluminescent material in organic flat panel display device.
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| CN1325478C (en) * | 2004-04-01 | 2007-07-11 | 复旦大学 | Nano structured organic photoelectric material, and preparation method |
| CN100395269C (en) * | 2004-07-09 | 2008-06-18 | 复旦大学 | Organic polymer material containing screw fluorene structure and its use |
| US7507351B2 (en) | 2003-06-05 | 2009-03-24 | Hitachi Chemical Co., Ltd. | Method for purifying electroluminescent material, electroluminescent material and electroluminescent device |
| CN100489057C (en) * | 2005-11-29 | 2009-05-20 | 中国科学院长春应用化学研究所 | Blue polyarylether high molecule electroluminescent material and its preparation method |
| US8075943B2 (en) | 2005-12-27 | 2011-12-13 | Hitachi Chemical Co., Ltd. | Purification process for organic electronics material |
| CN102443140A (en) * | 2010-10-09 | 2012-05-09 | 中国科学院化学研究所 | Reagent for detecting EGFR genetic mutation and application thereof |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7507351B2 (en) | 2003-06-05 | 2009-03-24 | Hitachi Chemical Co., Ltd. | Method for purifying electroluminescent material, electroluminescent material and electroluminescent device |
| CN1325478C (en) * | 2004-04-01 | 2007-07-11 | 复旦大学 | Nano structured organic photoelectric material, and preparation method |
| CN100395269C (en) * | 2004-07-09 | 2008-06-18 | 复旦大学 | Organic polymer material containing screw fluorene structure and its use |
| CN1295298C (en) * | 2004-12-08 | 2007-01-17 | 中国科学院长春应用化学研究所 | Blue color electroluminescent macromolecular material and method for making same |
| CN100489057C (en) * | 2005-11-29 | 2009-05-20 | 中国科学院长春应用化学研究所 | Blue polyarylether high molecule electroluminescent material and its preparation method |
| US8075943B2 (en) | 2005-12-27 | 2011-12-13 | Hitachi Chemical Co., Ltd. | Purification process for organic electronics material |
| CN102443140A (en) * | 2010-10-09 | 2012-05-09 | 中国科学院化学研究所 | Reagent for detecting EGFR genetic mutation and application thereof |
| CN102443140B (en) * | 2010-10-09 | 2013-09-04 | 中国科学院化学研究所 | Reagent for detecting EGFR genetic mutation and application thereof |
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